Nitric Acid → N-(4-(1,1-Dimethylethyl)-2-nitrophenyl)acetamide

HRID 742332Notes

Reaction equation

HRID 742332 reaction equation
[C:1]([C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[N+:12]([O-:15])(O)=[O:13].[C:16](OC(=O)C)(=[O:18])[CH3:17]>>[C:16]([NH:9][C:8]1[CH:7]=[CH:6][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:11][C:10]=1[N+:12]([O-:15])=[O:13])(=[O:18])[CH3:17]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 698614-Tert-Butylaniline

Product 1

HCID 97069N-(4-(1,1-Dimethylethyl)-2-nitrophenyl)acetamideYield 90%

Procedure

4-t-Butylaniline (5 g, 33.58 mmol) in acetic anhydride (25 ml) was stirred at ambient temperature for 0.5h. The mixture was cooled in an ice-bath and nitric acid (6 ml, 65%) was added at such a rate that the temperature did not exceed 18° C. Following the addition the mixture was poured on ice (200 g). The precipitate was filtered off, washed thoroughly with water and dried to yield N-acetyl-4-t-butyl-2-nitroaniline (7.15 g, 90%). Mp. 109°-110° C.

Workup

  1. temperatureThe mixture was cooled in an ice-bath
  2. customdid not exceed 18° C
  3. additionthe addition the mixture
  4. additionwas poured on ice (200 g)
  5. filtrationThe precipitate was filtered off
  6. washwashed thoroughly with water
  7. customdried

Sources & evidence

ORD record
ord-ab6407767a4d4a79b26c23a6c6651bde
Source dataset
uspto-grants-1996_09
Patent number
US05554630

Reaction notes

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