1-Butanol → 7-butoxy-3-butyl-5-methyl-3H-imidazo[4,5-b]pyridine-6-carboxylic acid, ethyl ester

HRID 371926Notes

Reaction equation

HRID 371926 reaction equation
[Na].[CH2:2]([OH:6])[CH2:3][CH2:4][CH3:5].[CH2:7]([N:11]1[C:15]2=[N:16][C:17]([CH3:26])=[C:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:19](Cl)=[C:14]2[N:13]=[CH:12]1)[CH2:8][CH2:9][CH3:10]>C1C=CC=CC=1>[CH2:2]([O:6][C:19]1[C:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:17]([CH3:26])[N:16]=[C:15]2[N:11]([CH2:7][CH2:8][CH2:9][CH3:10])[CH:12]=[N:13][C:14]=12)[CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 2631-ButanolHCID 5360545SodiumHCID 123876393-butyl-7-chloro-5-methyl-3H-imidazo[4,5-b]pyridine-6-carboxylic acid, ethyl ester

Product 1

HCID 123876437-butoxy-3-butyl-5-methyl-3H-imidazo[4,5-b]pyridine-6-carboxylic acid, ethyl ester

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

0.03 g. of sodium and 0.8 g. of n-butyl alcohol are refluxed for 5 hours in 50 ml. of dry benzene. After this time, 3 g. of 3-butyl-7-chloro-5-methyl-3H-imidazo[4,5-b]pyridine-6-carboxylic acid, ethyl ester obtained in Example 3 c are added and the mixture is refluxed for 12 hours. After the inorganic precipitate has been filtered off, the solvent is removed in vacuo and the residue distilled to obtain 7-butoxy-3-butyl-5-methyl-3H-imidazo[4,5-b]pyridine-6-carboxylic acid, ethyl ester, b.p. 210°-220°/0.01. Yield 2.1 g. (66%).

Workup

  1. temperaturethe mixture is refluxed for 12 hours
  2. filtrationAfter the inorganic precipitate has been filtered off
  3. customthe solvent is removed in vacuo
  4. distillationthe residue distilled

Sources & evidence

ORD record
ord-d53194f3cd824605ad82211816c83fab
Source dataset
uspto-grants-1978_05
Patent number
US04088654

Reaction notes

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