Hydrochloric Acid → 4-amino-2-chloro-N,N-dimethylbenzamide

HRID 1198201

반응식

HRID 1198201 반응식
O.Cl.[Cl:3][C:4]1[CH:14]=[C:13]([N+:15]([O-])=O)[CH:12]=[CH:11][C:5]=1[C:6]([N:8]([CH3:10])[CH3:9])=[O:7]>C(O)C.[Fe]>[NH2:15][C:13]1[CH:12]=[CH:11][C:5]([C:6]([N:8]([CH3:10])[CH3:9])=[O:7])=[C:4]([Cl:3])[CH:14]=1

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 32645532-chloro-N,N-dimethyl-4-nitrobenzamide

생성물 1

HCID 109434804-amino-2-chloro-N,N-dimethylbenzamide수율 80%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 702Ethanol용매

실험 절차

Iron powder (pre-reduced with hydrogen, 10.0 g) was suspended in ethanol (80ml) and water (10ml) and concentrated hydrochloric acid (4ml) were added with vigorous stirring. 2-Chloro-4-nitro-N,N-dimethylbenzamide (7.50 g) was added in small portions over 15 minutes and the mixture then heated to 50°-60° C. and stirred for 5 hours. The mixture was filtered through Celite and the ethanol evaporated. Water (200 ml) and concentrated hydrochloric acid (20 ml) were added and the reaction washed with ethyl acetate and then basified to pH8 with sodium bicarbonate and extracted with methylene chloride. The organic extract was dried and evaporated to give 4-amino-2-chloro-N,N-dimethylbenzamide as a grey crystalline solid (5.21 g) which was recrystallised from chloroform/ethyl acetate to give off-white crystals (3.46 g, m.p. 170° 173° C.).

후처리

  1. temperaturethe mixture then heated to 50°-60° C.
  2. filtrationThe mixture was filtered through Celite
  3. customthe ethanol evaporated
  4. additionWater (200 ml) and concentrated hydrochloric acid (20 ml) were added
  5. washthe reaction washed with ethyl acetate
  6. extractionextracted with methylene chloride
  7. extractionThe organic extract
  8. customwas dried
  9. customevaporated

출처 및 근거

ORD 기록
ord-d3404771b3be43fab6ae1680999708b3
출처 데이터셋
uspto-grants-1994_01
특허 번호
US05280044

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