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

HRID 1415135Notes

Reaction equation

HRID 1415135 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-8ed144ab778a4ded810e32e073fcd8f1
Source dataset
uspto-grants-1977_01
Patent number
US04003908

Reaction notes

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