Dimethylformamide → 2-Chloro-6-nitroaniline

HRID 1521642

反応式

HRID 1521642 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[CH:3]=1.CC(C)([O-])C.[K+].C[N:18](C)C=O>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[NH2:18]

参加物

4

反応物 3

HCID 6228Dimethylformamide2 回HCID 84891-Chloro-3-nitrobenzeneHCID 23665647Potassium tert-butoxide

生成物 1

HCID 698552-Chloro-6-nitroaniline

反応条件

温度
15 °C

実験手順

1-chloro-3-nitrobenzene (3.1 g, 0.0197 mol) and o-methoxylamine hydrochloride (2.02 g, 0.0236 mol) were dissolved in N,N-dimethylformamide (15 mL). The solution was added drop wise in 15 min to a suspension of cuprous chloride and potassium tert-butoxide (11.07 g, 0.965 mol) in N,N-dimethylformamide (15 mL) cooled in a 15° C. bath. The cold bath was removed; the mixture was allowed to come to RT and stirred for 1 h. The reaction was quenched with aqueous ammonium chloride solution and extracted with ethyl acetate (4×100 mL). The combined organic layer was washed with saturated aqueous sodium chloride solution, dried over sodium sulphate, concentrated under vacuum and purified by silica gel column chromatography to obtain the title compound. 1H NMR (400 MHz, CDCl3) δ 8.020-7.994 (dd, J=8.8 Hz, 10.4 Hz, 1H), 7.696-7.674 (dd, J=7.2 Hz, 8.8 Hz, 1H), 7.229 (bs, 1H), 6.705-6.664 (t, J=8.4 Hz, 1H).

後処理

  1. additionThe solution was added drop wise in 15 min
  2. customThe cold bath was removed
  3. customto come to RT
  4. customThe reaction was quenched with aqueous ammonium chloride solution
  5. extractionextracted with ethyl acetate (4×100 mL)
  6. washThe combined organic layer was washed with saturated aqueous sodium chloride solution
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated under vacuum
  9. custompurified by silica gel column chromatography

出典と根拠

ORDレコード
ord-98e81f5be4e347f789f39cc308130c60
出典データセット
uspto-grants-2015_07
特許番号
US09073929B2

関連ノート

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