Reaction #816373

ord-5b8e72a69e2f47ab8ec4826f10a43cbf

Reaction equation

Cc1c(N)c(=O)n(-c2ccccc2)n1C
4-amino-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one
CC(=O)Nc1cccc(O)c1
N-(3-hydroxyphenyl)acetamide
N
ammonia
→
CC(=O)NC1=CC(=O)C=C/C1=N\c1c(C)n(C)n(-c2ccccc2)c1=O
N-{(6E)-6-[(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)imino]-3-oxocyclohexa-1,4-dien-1-yl}acetamide

Reactants

Cc1c(N)c(=O)n(-c2ccccc2)n1C
4-amino-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one
CC(=O)Nc1cccc(O)c1
N-(3-hydroxyphenyl)acetamide
N
ammonia

Reagents

N#[C][Fe-3]([C]#N)([C]#N)([C]#N)([C]#N)[C]#N.[K+].[K+].[K+]
potassium ferricyanide

Solvents

O
water
CC(C)O
2-propanol

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherranging from 5 to 10° C.

Procedure

10 mmol of 4-amino-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one was dissolved in 30 ml of water. This solution was admixed with 10 mmol of N-(3-hydroxyphenyl)acetamide in solution in 30 ml of 2-propanol, 3 ml of 20% aqueous ammonia and 22 mmol of potassium ferricyanide at a temperature ranging from 5 to 10° C.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07582123B2uspto-grants-2009_09