Ethanol → 5-[(Ethoxy-methylene)amino]-1-methyl-1h-pyrazole-4-carboxylic acid, ethyl ester

HRID 1703622Notes

Reaction equation

HRID 1703622 reaction equation
[CH3:1][N:2]1[C:6]([NH2:7])=[C:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:4]=[N:3]1.[CH:13]([OH:16])(O)O.[CH2:17](O)[CH3:18]>>[CH2:17]([O:16][CH:13]=[N:7][C:6]1[N:2]([CH3:1])[N:3]=[CH:4][C:5]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:18]

Participants

4

Reactant 3

HCID 702EthanolHCID 271299Ethyl 5-amino-1-methyl-1H-pyrazole-4-carboxylateHCID 5231666Orthoformic acid

Product 1

HCID 867361415-[(Ethoxy-methylene)amino]-1-methyl-1h-pyrazole-4-carboxylic acid, ethyl esterYield 87%

Procedure

84.6 g. of 1-methyl-4-carboethoxy-5-aminopyrazole and 74.1 g. of orthoformic acid triethyul ester are heated together until the splitting off of ethanol has ended. The oily residue is distilled under oil pump vacuum to obtain 5-[(ethoxy-methylene)amino]-1-methyl-1h-pyrazole-4-carboxylic acid, ethyl ester b.p. 98°-102°; m.p. 32°-34° (yield87%).

Workup

  1. distillationThe oily residue is distilled under oil pump vacuum

Sources & evidence

ORD record
ord-776f3c41047e4bc2bc33d490672d8636
Source dataset
uspto-grants-1978_11
Patent number
US04124764

Reaction notes

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