Nitric Acid → 3-Acetamido-4-methyl-2-nitrobenzoic acid

HRID 968790

반응식

HRID 968790 반응식
[N+:1]([O-:4])(O)=[O:2].[C:5]([NH:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[CH3:18])[C:12]([OH:14])=[O:13])(=[O:7])[CH3:6].NC1C([N+]([O-])=O)=C(C)C([N+]([O-])=O)=CC=1C#N>>[C:5]([NH:8][C:9]1[C:10]([N+:1]([O-:4])=[O:2])=[C:11]([CH:15]=[CH:16][C:17]=1[CH3:18])[C:12]([OH:14])=[O:13])(=[O:7])[CH3:6]

참가 물질

4

반응물 3

HCID 944Nitric AcidHCID 2434323-Acetamido-4-methylbenzoic acidHCID 167267892-Amino-4-methyl-3,5-dinitrobenzonitrile

생성물 1

HCID 2434333-Acetamido-4-methyl-2-nitrobenzoic acid

반응 조건

온도
0 °C

실험 절차

Fuming nitric acid (100 mL, 2.4 mol) is cooled to about 0° C. (ice/acetone/water bath) and 3-(Acetylamino)-4-methylbenzoic Acid (14) (24.567 g, 127.2 mmol) is added in small portions over about 30 minutes, at rate to maintain the internal reaction temperature <5° C. The hetereogeneous reaction mixture is then stirred at about 0° C. for an additional 1 hour. The reaction mixture is then added to ice water (300 mL) and stirred for about 1 hour. The solid obtained is filtered and dried to provide a mixture of 3-N-acetyl-4-methyl-2-nitro benzoic acid (5) and 3-N-acetyl-4-methyl-5-nitro benzoic acid, in ratio of about 78:22 (27.79 g, 92% Combined Yield). A portion of this mixture (23.458 g) is recrystallized from acetic acid (300 mL) to give 3-(Acetylamino)-4-methyl-2-nitrobenzoic Acid (15), as a white solid (15.370 g, 51% yield).

후처리

  1. additionis added in small portions over about 30 minutes, at rate
  2. temperatureto maintain the internal reaction temperature <5° C
  3. stirringstirred for about 1 hour
  4. customThe solid obtained
  5. filtrationis filtered
  6. customdried
  7. customto provide
  8. customin ratio of about 78:22 (27.79 g, 92% Combined Yield)
  9. customA portion of this mixture (23.458 g) is recrystallized from acetic acid (300 mL)

출처 및 근거

ORD 기록
ord-bbcd564821964a078314caf03b648d3a
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07304084B2

연결된 노트

불러오는 중…