Reaction #816375

ord-025a511458114e689c858c6d71844f4b

Reaction equation

Cc1c(N)c(=O)n(-c2ccccc2)n1C
4-amino-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one
Cc1cccc(O)c1
meta-cresol
N
ammonia
→
CC1=CC(=O)C=C/C1=N/c1c(C)n(C)n(-c2ccccc2)c1=O
1,5-dimethyl-4-{[(1Z)-2-methyl-4-oxocyclohexa-2,5-dien-1-ylidene]amino}-2-phenyl-1,2-dihydro-3H-pyrazol-3-one

Reactants

Cc1c(N)c(=O)n(-c2ccccc2)n1C
4-amino-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one
Cc1cccc(O)c1
meta-cresol
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 meta-cresol 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