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

HRID 359049

Reaction equation

HRID 359049 reaction equation
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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

Iron powder (pre-reduced with hydrogen, 10.0 g) was suspended in ethanol (80 ml) and water (10 ml) and concentrated hydrochloric acid (4 ml) 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.).

Workup

  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

Sources & evidence

ORD record
ord-68c8143dd2d6430eaa798df8ebbbc439
Source dataset
uspto-grants-1991_03
Patent number
US04999381

Linked notes

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