Water → 4-Amino-3-chloro-5-nitro-2-phenylamino-benzoic acid methyl ester

HRID 216494

반응식

HRID 216494 반응식
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[C:7]([NH2:13])=[C:6]([Cl:14])[C:5]=1F.[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>CO>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[C:7]([NH2:13])=[C:6]([Cl:14])[C:5]=1[NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 6115AnilineHCID 858681944-Amino-3-chloro-2-fluoro-5-nitro-benzoic acid methyl ester

생성물 1

HCID 858681964-Amino-3-chloro-5-nitro-2-phenylamino-benzoic acid methyl ester수율 84.4%

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
0 °C

실험 절차

4-Amino-3-chloro-2-fluoro-5-nitro-benzoic acid methyl ester 4a (2.20 g, 8.84 mmol) is suspended in MeOH (9.4 mL) and aniline (3.22 mL, 35.4 mmol) is added. The reaction mixture is heated to reflux with stirring under a nitrogen atmosphere. After 19 hours, the reaction is complete. Distilled water (3.22 mL) is added to the reaction mixture and refluxing is continued for one hour. The reaction mixture is cooled to 0° C. in an ice bath for 20 minutes. The reaction mixture is filtered and washed with 3:10 distilled water/MeOH (65 mL total) and then with MeOH. The solid is dissolved with CH2Cl2 and concentrated under reduced pressure to give 2.40 g (84%) of pure desired product. MS APCI (−) m/z 320.3 (M−1) detected.

후처리

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux
  3. temperaturerefluxing
  4. waitis continued for one hour
  5. filtrationThe reaction mixture is filtered
  6. washwashed with 3:10 distilled water/MeOH (65 mL total)
  7. dissolutionThe solid is dissolved with CH2Cl2
  8. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-15eda21fdba146a7a43f84f9530168ed
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193229B2

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