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ChemicalBook--->CAS DataBase List--->86499-96-9

86499-96-9

86499-96-9 Structure

86499-96-9 Structure
IdentificationMore
[Name]

3-Bromo-2,3,4,5-tetrahydro-2H-benzo[b]azepin-2-one
[CAS]

86499-96-9
[Synonyms]

3-bromo-1,3,4,5-tetrahdro-2h-benzazepin-2-one
3-BROMO-1,3,4,5-TETRAHYDRO-2H-1-BENZAZEPIN-2-ONE
3-BROMO-1,3,4,5-TETRAHYDRO-2H-1-BENZAZEPINE-2-ONE
3-BROMO-1,3,4,5-TETRAHYDRO-2H-L-BENZAZEPIN-2-ONE
3-BROMO-1,3,4,5-TETRAHYDRO-BENZO[B]AZEPIN-2-ONE
3-BROMO-2,3,4,5-TETRAHYDRO-1H-1-BENZAZEPINE-2-ONE
3-BROMO-2,3,4,5-TETRAHYDRO-2H-1-BENZAZEPIN-2-ONE
3-BROMO-2,3,4,5-TETRAHYDRO-2H-BENZO[B]AZEPIN-2-ONE
3-BROMO-2,3,4,5-TETRAHYDRO-2-OXO-1H-1-BENZAZEPINE
3-BROMO-2,3,4,5-TRTRAHYDRO-2H-1-BENZAZEPINE-2-ONE
3-bromobenzocaprolactam
A-BROMOBENZOCAPROLACTAM
ALPHA-BROMOBENZO-CAPROLACTAM
3-BromoTetrahydrobenazepin-2-One
3-BROMO-1,3,4,5-TETRAHYDRO-2H-BENZAZEPIN-2-ONE
3-BROMO-1,3,4,5-TETRAHYDRO-2H-1-BENZAEPINE-2-ONE
3-BBC: 3-BROMO-2,3,4,5-TETRAHYDRO-1H-1-BENZAZEPIN-2-ONE
3-BROMO-2,3,4,5-TETRAHYDRO-2H-1-BENZAZEPINE-2-ONE
3-Bromo-2,3,4,5-tetrahydro-2H-
3-BROMO-1,3,4,5-TETRAHYDRO-2H-1-BENZAZEPINE-2-ONE HPLC +99.0%
[Molecular Formula]

C10H10BrNO
[MDL Number]

MFCD03085918
[Molecular Weight]

240.1
[MOL File]

86499-96-9.mol
Chemical PropertiesBack Directory
[Melting point ]

164 °C
[Boiling point ]

383.2±42.0 °C(Predicted)
[density ]

1.492±0.06 g/cm3(Predicted)
[Fp ]

185.542℃
[storage temp. ]

Keep in dark place,Sealed in dry,Room Temperature
[solubility ]

slightly soluble in ethanol, benzene, acetone, insoluble in water
[pka]

13.59±0.40(Predicted)
[Appearance]

Off-white to light yellow Solid
[InChI]

InChI=1S/C10H10BrNO/c11-8-6-5-7-3-1-2-4-9(7)12-10(8)13/h1-4,8H,5-6H2,(H,12,13)
[InChIKey]

JMXPGCGROVEPID-UHFFFAOYSA-N
[SMILES]

N1C2=CC=CC=C2CCC(Br)C1=O
[CAS DataBase Reference]

86499-96-9(CAS DataBase Reference)
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H315-H319
[Precautionary statements ]

P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313
Hazard InformationBack Directory
[Uses]

3-Bromo-1,3,4,5-tetrahydro-2H-benzo[b]azepin-2-one is an intermediate in the synthesis of Benazepril Hydrochloride. Benazepril Hydrochloride is a first-line antihypertensive drug recommended by the WHO. It is a chiral drug with excellent clinical efficacy, strong safety and tiny side effects in the international antihypertensive drugs of angiotensin converting enzyme inhibitors.
[Chemical Properties]

White or almost white crystalline
[Preparation]

The preparation of 3-Bromo-1,3,4,5-tetrahydro-2H-benzo[b]azepin-2-one is as follows:10 parts by weight of the heated melted polyphosphoric acid was added to the drying kettle, With stirring, The above 2-bromo-3,4-dihydro-N-hydroxy- (2H) -naphthalimide was added in portions at a temperature of 60 ° C, Insulation reaction for 20 hours; The reaction solution was added dropwise to 12.5 parts by weight of water to carry out hydrolysis, Still Washed to give 3-bromo-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one crude; 10 parts by weight of methanol and 0.1 part by weight of activated carbon were added, Heating decolorization, After filtration, the filtrate was cooled to 10 ° C for 20 hours, centrifuged, washed and dried to give 3-bromo-1,3,4,5-tetrahydro-2H-1-benzazepan-2-one. The purity of the product was 3, 10-bromo-1,3,4,5-tetrahydro-2H-1-benzazepan-2-one as high as 99.6% and the yield was as high as 98%.

86499-96-9.png

[Synthesis]

1,3,4,5-Tetrahydro-2H-1-benzazepin-2-one

4424-80-0

3-Bromo-1,3,4,5-tetrahydro-2H-benzo[b]azepin-2-one

86499-96-9

General procedure for the synthesis of 3-bromo-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one from 1,3,4,5-tetrahydro-2H-1-benzazepin-2-one: 1,3,4,5-tetrahydro-2H-1-benzazepin-2-one (1.0 g, 6.20 mmol) was dissolved in anhydrous CHCl3 (15 ml) and cooled to 0 °C ( ice-salt bath). Under argon protection, PCl5 (1.5 g, 7.20 mmol) and I2 (15 mg) were added and stirred at 0 °C for 30 min. Subsequently, Br2 (0.39 ml, 7.51 mmol) was added dropwise to the reaction solution, which was slowly warmed to room temperature and refluxed for 4.0 h under argon protection. After completion of the reaction, the mixture was poured into ice water (20 g) and the organic and aqueous phases were separated after thorough stirring. The aqueous phase was extracted with CHCl3 (25 ml), the organic phases were combined, washed with H2O (5.0 ml), dried over anhydrous MgSO4, filtered and concentrated to dryness, and dried under vacuum to give the crude product. The crude product was purified by silica gel column chromatography (Merck, 70 g) with EtOAc: hexane (1:9) as eluent to afford 3-bromo-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one as an off-white solid (1.137 g, 70.1% yield, melting point 170-172 °C). The structure of the product was confirmed by 1H-NMR and 13C-NMR. TLC detection: Rf 0.13 (silica gel plate, EtOAc:hexane=1:4, observed under UV light).

[References]

[1] Patent: US6777550, 2004, B1. Location in patent: Page column 28
[2] Patent: US4575503, 1986, A
[3] Patent: US4410520, 1983, A
[4] Patent: US4473575, 1984, A
[5] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 17, p. 3488 - 3494
Spectrum DetailBack Directory
[Spectrum Detail]

3-Bromo-1,3,4,5-tetrahydro-2H-benzo[b]azepin-2-one(86499-96-9)1HNMR
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