Ethyl orthoformate → 7-chloro-3-ethyl-5-methyl-3H-imidazo[4,5-b]pyridine-6-carboxylic acid, ethyl ester

HRID 2071616Notes

Reaction equation

HRID 2071616 reaction equation
[NH2:1][C:2]1[C:3]([Cl:17])=[C:4]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:5]([CH3:11])=[N:6][C:7]=1[NH:8][CH2:9][CH3:10].[CH2:18](OC(OCC)OCC)C>>[Cl:17][C:3]1[C:4]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:5]([CH3:11])[N:6]=[C:7]2[N:8]([CH2:9][CH3:10])[CH:18]=[N:1][C:2]=12

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 123876185-Amino-6-ethylamino-4-chloro-2-methylpyridine-3-carboxylic acid, ethyl ester

Product 1

HCID 123876387-chloro-3-ethyl-5-methyl-3H-imidazo[4,5-b]pyridine-6-carboxylic acid, ethyl ester

Procedure

25.7 g. of 5-amino-6-ethylamino-4-chloro-2-methylpyridine-3-carboxylic acid, ethyl ester (0.1 mol.) is refluxed for 12 hours with 100 ml. of orthoformic acid triethyl ester with stirring. The excess ester is removed in vacuo and the oily residue distilled to obtain 7-chloro-3-ethyl-5-methyl-3H-imidazo[4,5-b]pyridine-6-carboxylic acid, ethyl ester, b.p. 195°/0.01. Yield 23 g. (86%).

Workup

  1. customThe excess ester is removed in vacuo
  2. distillationthe oily residue distilled

Sources & evidence

ORD record
ord-db2567df93924af1bca6db31fd2f578a
Source dataset
uspto-grants-1977_09
Patent number
US04048182

Reaction notes

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