4-Nitroaniline → Butanamide, 3,3-dimethyl-N-(4-nitrophenyl)-

HRID 483097Notes

Reaction equation

HRID 483097 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:11][C:12]([CH3:18])([CH3:17])[CH2:13][C:14](Cl)=[O:15]>N1C=CC=CC=1>[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH:8][C:14](=[O:15])[CH2:13][C:12]([CH3:18])([CH3:17])[CH3:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 74754-NitroanilineHCID 815143,3-Dimethylbutanoyl chloride

Product 1

HCID 2924068Butanamide, 3,3-dimethyl-N-(4-nitrophenyl)-Yield 73.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Five grams of 4-nitroaniline was stirred in 25 ml of pyridine and 4.95 g of 3,3-dimethylbutyryl chloride was added. The mixture was stirred 15 hours and poured into ice-water. The resultant solid was collected on a filter and dissolved in 200 ml of ethyl acetate and the solution was treated with activated charcoal and concentrated to yield 6.3 g of 4-nitro-3,3-dimethylbutyrylaminobenzene, m.p. 192°-194°. This material was reduced in 200 ml of methanol, at 3 atmospheres of hydrogen in the presence of 5% Pd/carbon. After removal of the catalyst by filtration, concentration of the filtrate gives 5.3 g of product (3,3-dimethylbutyrylamino)aniline, m.p. 138°-140° C.

Workup

  1. customThe resultant solid was collected on
  2. filtrationa filter
  3. dissolutiondissolved in 200 ml of ethyl acetate
  4. additionthe solution was treated with activated charcoal
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-aab990405b724fe1b6d04dd0e1b40daa
Source dataset
uspto-grants-1986_03
Patent number
US04578390

Reaction notes

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