Phenylacetonitrile → 3-Pyrazolecarboxylic acid, 4-amino-5-phenyl-, ethyl ester

HRID 1693526Notes

Reaction equation

[CH2:1]([C:8]#[N:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:10](=[CH:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N-:11]>>[CH2:16]([O:15][C:13]([C:12]1[NH:10][N:11]=[C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:8]=1[NH2:9])=[O:14])[CH3:17]

Participants

Reactant 2

HCID 8794Phenylacetonitrile

HCID 12192Ethyl diazoacetate

Product 1

HCID 30534813-Pyrazolecarboxylic acid, 4-amino-5-phenyl-, ethyl ester

Procedure

4-Amino-5-phenyl-2H-pyrazole-3-carboxylic acid ethyl ester is prepared from benzyl cyanide and ethyl diazoacetate, using the condition described in Rochais, C.; Lisowski, V.; Dellemagne, P.; Rault, S. Tetrahedron Lett. 2004, 45, 6353. HPLC-MS calculated for C12H13N3O2 (M+H+) 232.1. Found: 232.2.

Sources & evidence

ORD record: ord-00ee26b73482468dbe1d260e4bdbc9b5
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08158634B2

Reaction notes

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