ChemicalBook CAS DataBase List 4-Methyl-2-n-propyl-1H-benzimidazole-6-carboxylic acid

4-Methyl-2-n-propyl-1H-benzimidazole-6-carboxylic acid synthesis

10synthesis methods

Product Name:4-Methyl-2-n-propyl-1H-benzimidazole-6-carboxylic acid
CAS Number:152628-03-0
Molecular formula:C12H14N2O2
Molecular Weight:218.25

Methyl 4-(butyrylamino)-3-methyl-5-nitrobenzoate

152628-01-8

4-Methyl-2-n-propyl-1H-benzimidazole-6-carboxylic acid

152628-03-0

Example 4: Methyl 3-methyl-4-butyrylamino-5-nitrobenzoate (II) (10 g, 0.036 mol) was suspended in 60 ml of water and heated to 70-80 °C. A suspension of sodium dithionite (21.75 g, 0.124 mol) in 60 ml of water was added slowly and heated to 90-100 °C. Upon completion of the reaction, the pH of the reaction mixture was adjusted to 10-11 and the temperature was maintained with continued stirring until TLC detection showed complete disappearance of methyl 3-methyl-4-butyrylamino-5-nitrobenzoate. Subsequently, the pH of the reaction mixture was adjusted to 6-6.5. The resulting solid was filtered and dried at 45-50 °C to afford 2-n-propyl-4-methyl-6-carboxybenzimidazole (7.5 g, yield: 96.4%).

152628-01-8 Synthesis

152628-01-8
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152628-03-0
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Yield:152628-03-0 96.4%

Reaction Conditions:

with sodium dithionite;water at 70 - 100;

Steps:

II.4

Example 4:4-butyramido-3-methyl-5-nitro methyl benzoate (II) (10 gm, 0.036 moles), was suspended in water (60 ml) and heated to 70-80 °C. A suspension of sodium dithionite (21.75 gm, 0.124 moles) in water (60 ml) was added gradually to the above mass and the temperature is raised to 90-100 °C. After the reaction complies, the pH of the reaction mixture was adjusted to 10-11 and continued to stir at same temperature until the methyl-4-methyl-2-propyl-lH-benzimidazole-6-carboxylate disappears in TLC. Then the pH of the reaction mass adjusted to pH 6-6.5. The solid obtained was filtered and dried at 45-50 °C to afford 2-n-propyl-4-methyl-6- carboxy benzimidazole (7.5 gms, Yield: 96.4 %).

References:

WO2012/28925,2012,A2 Location in patent:Page/Page column 18

201230-82-2 Synthesis