Pyridine → 2-(4-Tert-butylbenzoylamino)-5-nitrobenzoic acid

HRID 395714

반응식

HRID 395714 반응식
[N+:1]([C:4]1[CH:12]=[C:8]([C:9]([OH:11])=[O:10])[C:7]([NH2:13])=[CH:6][CH:5]=1)([O-:3])=[O:2].N1C=CC=CC=1.[C:20]([C:24]1[CH:32]=[CH:31][CH:30]=[CH:29][C:25]=1C(Cl)=O)([CH3:23])([CH3:22])[CH3:21].CN(C)[CH:35]=[O:36]>>[C:20]([C:24]1[CH:25]=[CH:29][C:30]([C:35]([NH:13][C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][C:8]=2[C:9]([OH:11])=[O:10])=[O:36])=[CH:31][CH:32]=1)([CH3:21])([CH3:22])[CH3:23]

참가 물질

5

반응물 4

HCID 1049PyridineHCID 6228DimethylformamideHCID 120322-Amino-5-nitrobenzoic acidHCID 137671862-tert-Butylbenzoyl chloride

생성물 1

HCID 104974752-(4-Tert-butylbenzoylamino)-5-nitrobenzoic acid수율 80%

반응 조건

온도
0 °C

실험 절차

To a mixture of 5-nitroanthranilic acid (24.6 g, 135 mmol) and pyridine (14.2 mL, 175 mmol) in N,N-dimethylformamide (140 mL) cooled to 0° C. was added tert-butylbenzoyl chloride (31.6 mL, 162 mmol). After stirring for 1 h, the reaction mixture was heated at 75° C. for 4 h, cooled, and poured into an ice/water mixture. The resulting solid was filtered, washed with water and a 1:2 mixture of diethyl ether/hexanes, and dried in vacuo at 150° C. for 2 h to give 37.1 g (80%) of the title compound as a light brown solid; mp 245-9° C. MS-FD m/e 342 (p) Analysis for C18H18N2O5: Calc: C, 63.15; H, 5.30; N, 8.18; Found: C, 62.85; H, 5.05; N, 8.48.

후처리

  1. temperaturethe reaction mixture was heated at 75° C. for 4 h
  2. temperaturecooled
  3. filtrationThe resulting solid was filtered
  4. washwashed with water
  5. additiona 1:2 mixture of diethyl ether/hexanes
  6. customdried in vacuo at 150° C. for 2 h

출처 및 근거

ORD 기록
ord-fa28e41d3d124130856f4769c30f5c29
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06605626B2

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