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

HRID 424862Notes

Reaction equation

HRID 424862 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([NH:8][CH3:9])[CH:7]=1.[NH2:13][C:14]1[C:19]([CH3:20])=[CH:18][C:17]([OH:21])=[CH:16][C:15]=1[CH3:22].CC(C)([O-])C.[K+].O>CN(C)C(=O)C>[NH2:13][C:14]1[C:19]([CH3:20])=[CH:18][C:17]([O:21][C:2]2[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([NH:8][CH3:9])[CH:7]=2)=[CH:16][C:15]=1[CH3:22]

Participants

6

Reactant 4

HCID 962WaterHCID 765434-Amino-3,5-dimethylphenolHCID 2580415-chloro-N-methyl-2-nitroanilineHCID 23665647Potassium tert-butoxide

Product 1

HCID 667016652,6-Dimethyl-4-[3-(methylamino)-4-nitrophenoxy]anilineYield 80.7%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of N-(5-chloro-2-nitrophenyl)-N-methylamine (4.0 g) in N,N-dimethylacetamide (56 ml) were added 4-amino-3,5-dimethylphenol (2.9 g) and potassium t-butoxide (2.9 g) with stirring under ice-cooling, and the resulting mixture was stirred at 75-80° C. for 1 hour. After stirring, water (74 ml) was added to the reaction mixture, and the resulting mixture was cooled gradually to room temperature. The crystals precipitated were collected by filtration and dried in vacuo to afford the title compound (4.9 g, yield: 80%) as a yellow crystalline solid.

Workup

  1. temperaturecooling
  2. stirringthe resulting mixture was stirred at 75-80° C. for 1 hour
  3. stirringAfter stirring
  4. customThe crystals precipitated
  5. filtrationwere collected by filtration
  6. customdried in vacuo

Sources & evidence

ORD record
ord-bed30020c5a2485d9e0d88bee89b5d54
Source dataset
uspto-grants-2012_01
Patent number
US08106079B2

Reaction notes

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