4,5-Dimethyl-1,2-phenylenediamine → HCID 178428586, compound

HRID 2064664Notes

Reaction equation

[N+:1]([C:4]1[C:5]([C:9]([OH:11])=O)=[N:6][NH:7][CH:8]=1)([O-:3])=[O:2].[NH2:12][C:13]1[CH:18]=[C:17]([CH3:19])[C:16]([CH3:20])=[CH:15][C:14]=1[NH2:21]>[OH-].[NH4+]>[NH2:12][C:13]1[CH:18]=[C:17]([CH3:19])[C:16]([CH3:20])=[CH:15][C:14]=1[NH:21][C:9]([C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:8][NH:7][N:6]=1)=[O:11]

Participants

Conditions

Temperature: 70 °C

Procedure

Method B Polyphosphoric acid (500 g) was added to a 1 L flask equipped with an overhead stirrer and heated to 70° C. under nitrogen. A blended mixture of 4-nitro-3-pyrazole carboxylic acid (50 g) and 1,2-diamino-4,5-dimethylbenzene (43.4 g) was added and the mixture was heated to 180° C. After 1 hour at this temperature the reaction mixture was cooled to 130° C. and poured into ice water (2.5 kg). This mixture was stirred with an overhead stirrer and then treated with aqueous ammonium hydroxide (350 mL, 30%) until the pH was 2.1. After stirring for a further 15 minutes the mixture was filtered and the filtered solid was washed three times with water (200 mL) then dried under vacuum to give 4-nitro-1H-pyrazole-3-carboxylic acid (2-amino-4,5-dimethylphenyl)amide as a brown solid.

Workup

customequipped with an overhead stirrer
additionwas added
temperaturethe mixture was heated to 180° C
temperatureAfter 1 hour at this temperature the reaction mixture was cooled to 130° C.
stirringAfter stirring for a further 15 minutes the mixture
filtrationwas filtered
washthe filtered solid was washed three times with water (200 mL)
customthen dried under vacuum

Sources & evidence

ORD record: ord-ff5c2f5df84147af935e2f7761d220a1
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288425B2

Reaction notes

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