| Identification | Back Directory | [Name]
2-Hydroxynicotinaldehyde | [CAS]
36404-89-4 | [Synonyms]
2-Hydroxynicotinaldehyde
2-Hydroxynicotinaldehyde 97%
2-hydroxypyridine-3-carbaldehyde
2-oxo-1H-pyridine-3-carbaldehyde
2-keto-1H-pyridine-3-carbaldehyde
2-Hydroxypyridine-3-carboxaldehyde
2-oxo-1H-pyridine-3-carboxaldehyde
2-OXO-1,2-DIHYDRO-3-PYRIDINECARBALDEHYDE
2-Oxo-1,2-dihydropyridine-3-carbaldehyde
1,2-dihydro-2-oxo-3-Pyridinecarboxaldehyde
3-Pyridinecarboxaldehyde, 1,2-dihydro-2-oxo-
2-Hydroxynicotinaldehyde ISO 9001：2015 REACH | [Molecular Formula]
C6H5NO2 | [MDL Number]
MFCD07698588 | [MOL File]
36404-89-4.mol | [Molecular Weight]
123.11 |
| Chemical Properties | Back Directory | [Melting point ]
220-222° | [Boiling point ]
50 °C(Press: 80 Torr) | [density ]
1.365±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C | [form ]
powder or crystals | [pka]
10.18±0.10(Predicted) | [Appearance]
White to light yellow Solid | [InChI]
InChI=1S/C6H5NO2/c8-4-5-2-1-3-7-6(5)9/h1-4H,(H,7,9) | [InChIKey]
DNTYEVWEOFZXFE-UHFFFAOYSA-N | [SMILES]
C1(=O)NC=CC=C1C=O |
| Hazard Information | Back Directory | [Uses]
This reagent was used as a catalytic transient directing group by Jin-Quan Yu′s lab for Pd(II)-catalyzed γ-C(sp3)-H arylation to couple free primary amines with aryl iodides. Reactions included Pd(OAc)2 683124 and low catalyst and directing group loading. | [reaction suitability]
reaction type: C-C Bond Formation
reagent type: catalyst
reagent type: ligand
reaction type: C-H Activation | [Synthesis]
General procedure for the synthesis of 2-hydroxynicotinaldehyde from 2-chloro-3-pyridinecarboxaldehyde: 2-chloro-3-pyridinecarboxaldehyde (0.283 g, 2.00 mmol) was suspended in 3 M aqueous hydrochloric acid solution (2 mL). Four drops of 3% hydrogen peroxide solution were added and the mixture was placed in a sealed vial and microwaved at 100 °C for 2 hours. After the reaction was completed, it was cooled to room temperature and the product began to crystallize. The suspension was neutralized by addition of solid potassium carbonate. The precipitate was separated by filtration and recrystallized with a minimum volume of ethanol to give 2-hydroxynicotinaldehyde (0.190 g, 77% yield). The melting point was 224-225 °C (literature value: 224 °C).1H NMR (300 MHz, DMSO-d6) δ 12.37 (broad peak, 1H), 10.05 (d, J = 0.7 Hz, 1H), 7.95 (ddd, J = 7.1, 2.3 Hz, 1H), 7.80 (ddd, J = 6.3, 2.3 Hz, 1H), 6.36 ( ddd, J = 7.1, 6.3, 0.7 Hz, 1H). 13C NMR (75 MHz, DMSO-d6) δ 189.0, 162.0, 143.4, 142.6, 124.2, 105.3. | [References]
[1] Tetrahedron, 2010, vol. 66, # 14, p. 2761 - 2767
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1990, # 9, p. 2409 - 2415
[3] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 14, p. 3933 - 3937 |
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