Dimethyl malonate → 1-(4-Amino-2-chlorophenyl)ethan-1-one

HRID 1097932노트

반응식

HRID 1097932 반응식
[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].ClC1C=C([N+]([O-])=O)C=CC=1C(Cl)=O.COC(=O)CC(OC)=O>C(O)C.[Fe].C(Cl)Cl.O>[NH2:10][C:8]1[CH:7]=[CH:6][C:5]([C:13](=[O:15])[CH3:14])=[C:4]([Cl:3])[CH:9]=1

참가 물질

9

반응물 4

HCID 7943Dimethyl malonateHCID 25517Ammonium ChlorideHCID 81522Benzoyl chloride, 2-chloro-4-nitro-HCID 3143022'-Chloro-4'-nitroacetophenone

생성물 1

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

시약·촉매·용매 4

HCID 23925Iron촉매HCID 702Ethanol용매HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

Iron (2.7 g), ammonium chloride (2.6 g) and water (8.1 ml) were added to a solution of 1-(2-chloro-4-nitro-phenyl)-ethanone ([CAS Reg. No. 67818-41-1], 960 mg) in ethanol (68 ml), which was made from 2-chloro-4-nitro-benzoyl chloride and malonic acid dimethyl ester according to a procedure from Dai et al.; J. Med. Chem. 2005, 48, 6066. The mixture was heated 1 h under reflux. DCM (35 ml) was added, stirred for 2 min and filtered over Celite. The residue was washed with DCM (50 ml). Water (100 ml) was added to the combined organic layers, and then extracted with DCM. The combined organic layers were dried over Na2SO4 and concentrated in vacuo to give the title compound (837 mg) as light yellow oil, which was used in the next step without further purification. MS (m/e)=170.1 [M+H+].

후처리

  1. temperatureThe mixture was heated 1 h
  2. temperatureunder reflux
  3. filtrationfiltered over Celite
  4. washThe residue was washed with DCM (50 ml)
  5. additionWater (100 ml) was added to the combined organic layers
  6. extractionextracted with DCM
  7. dry with materialThe combined organic layers were dried over Na2SO4
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-e73763f28760440db2f0682768c691ec
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08143280B2

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