Dichloromethane → 1-(4-Amino-2-chlorophenyl)ethan-1-one

HRID 1095910Notes

Reaction equation

HRID 1095910 reaction equation
[Cl-].[NH4+].[Cl:3][C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[CH:6][C:5]=1[C:13](=[O:15])[CH3:14].C(Cl)Cl>C(O)C.O.[Fe]>[NH2:10][C:8]1[CH:7]=[CH:6][C:5]([C:13](=[O:15])[CH3:14])=[C:4]([Cl:3])[CH:9]=1

Participants

7

Reactant 3

HCID 6344DichloromethaneHCID 25517Ammonium ChlorideHCID 3143021-(2-chloro-4-nitrophenyl)ethanone

Product 1

HCID 127338371-(4-Amino-2-chlorophenyl)ethan-1-one

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Iron (2.7 g) and ammonium chloride (2.6 g) were added to a solution of 2′-chloro-4′-nitroacetophenone (CAS Reg. No. 67818-41-1, 960 mg) in ethanol (68 ml) and water (8.1 ml). The mixture was heated for 1 h under reflux. DCM (35 ml) was added and stirred for 2 min. The mixture was filtered over Celite. Water (100 ml) was added and extracted with DCM (200 ml, and 2×150 ml). The combined organic layers were dried over Na2SO4 and concentrated to give the title compound (837 mg) as light yellow oil. MS (m/e)=170.1 [M+H+].

Workup

  1. temperatureThe mixture was heated for 1 h
  2. temperatureunder reflux
  3. filtrationThe mixture was filtered over Celite
  4. additionWater (100 ml) was added
  5. extractionextracted with DCM (200 ml, and 2×150 ml)
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2d41fd8bbe664867a574c7e2145e5354
Source dataset
uspto-grants-2012_03
Patent number
US08138189B2

Reaction notes

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