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

HRID 1198201

Reaktionsgleichung

Reaktionsgleichung von HRID 1198201
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

Komponenten

6

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

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.).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-d3404771b3be43fab6ae1680999708b3
Quelldatensatz
uspto-grants-1994_01
Patentnummer
US05280044

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