Methylamine → 2,6-Dimethyl-4-[3-(methylamino)-4-nitrophenoxy]aniline

HRID 424866Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6](Cl)[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH3:12][NH2:13].[NH2:14][C:15]1[C:20]([CH3:21])=[CH:19][C:18]([OH:22])=[CH:17][C:16]=1[CH3:23].CC(C)([O-])C.[K+]>CN(C)C(=O)C.O>[NH2:14][C:15]1[C:20]([CH3:21])=[CH:19][C:18]([O:22][C:6]2[CH:5]=[CH:4][C:3]([N+:9]([O-:11])=[O:10])=[C:2]([NH:13][CH3:12])[CH:7]=2)=[CH:17][C:16]=1[CH3:23]

Participants

Conditions

Temperature: 77.5 °C

Procedure

To a solution of 2,4-dichloronitrobenzene (3.0 g) in N,N-dimethylacetamide (30 ml) was added a 40% aqueous solution of methylamine (4.9 g) at room temperature, and the resulting mixture was stirred at 75-80° C. for 1.5 hours. To the reaction mixture were added 4-amino-3,5-dimethylphenol (2.2 g), potassium t-butoxide (3.5 g), and N,N-dimethylacetamide (15 ml), and the resulting mixture was stirred at the same temperature for 3 hours. After stirring, water (60 ml) was added to the reaction mixture, and the resulting mixture was cooled gradually to room temperature. The crystalline solid precipitated was collected by filtration and dried in vacuo to afford the title compound (3.0 g, yield: 67%) as a yellow crystalline solid.

Workup

stirringthe resulting mixture was stirred at the same temperature for 3 hours
stirringAfter stirring
temperaturethe resulting mixture was cooled gradually to room temperature
customThe crystalline solid precipitated
filtrationwas collected by filtration
customdried in vacuo

Sources & evidence

ORD record: ord-60ec85ea250846e98d6e30b990b75e47
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106079B2

Reaction notes

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