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

HRID 216494

反応式

HRID 216494 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-15eda21fdba146a7a43f84f9530168ed
出典データセット
uspto-grants-2012_06
特許番号
US08193229B2

関連ノート

読み込み中…