2-Amino-5-Nitrophenol → 1H-Pyrazol-5-ol, 3-methyl-1-phenyl-

HRID 1391202Notes

Reaction equation

HRID 1391202 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([NH2:11])=[C:8]([OH:10])[CH:9]=1)([O-:3])=[O:2].[C:12]1([N:18]2[C:22](=[O:23])[CH:21]=[C:20]([CH2:24]S(O)(=O)=O)[NH:19]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>[Cr].O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([NH2:11])=[C:8]([OH:10])[CH:9]=1)([O-:3])=[O:2].[C:12]1([N:18]2[C:22](=[O:23])[CH:21]=[C:20]([CH3:24])[NH:19]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 2

HCID 49847212-Amino-5-NitrophenolHCID 20525502HCID 20525502, compound

Product 2

HCID 703351H-Pyrazol-5-ol, 3-methyl-1-phenyl-HCID 49847212-Amino-5-Nitrophenol

Reagents, catalysts & solvents 2

HCID 23976ChromiumCatalystHCID 962WaterSolvent

Procedure

44.0 Parts of the 1:1 chromium complex (obtained by the known process and containing 1 atom of chromium for each molecule of monoazo dyestuff) of the azo dyestuff from diazotised 5-nitro-2-amino-1-hydroxybenzene and 1-phenyl-3-sulphomethyl-5-pyrazolone are stirred together in 1000 parts of hot water with 33.9 parts of the monoazo dyestuff obtained by the known process from diazotised 5-nitro-2-amino-1-hydroxybenzene and 1-phenyl-3-methyl-5-pyrazolone. The suspension is adjusted to a pH of 7 to 8 by addition of 20 parts by volume of concentrated sodium hydroxide solution and subsequently stirred at 90°-95° C. until both starting dyestuffs can no longer be detected. The unitary chromium mixed complex present in the clear solution is precipitated by addition of sodium chloride, isolated by filtration, washed with sodium chloride solution, and then dried in vacuo. After it has been ground, the dyestuff is in the form of a red, readily water-soluble powder and from a bath containing ammonium sulphate dyes wool or polyamide fibres in full red shades with good fastness properties. It has the following constitution: ##STR12##

Workup

  1. custom44.0 Parts of the 1:1 chromium complex (obtained by the known process

Sources & evidence

ORD record
ord-185b7d0a8a9643a58f803e4822ad7181
Source dataset
uspto-grants-1979_02
Patent number
US04141890

Reaction notes

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