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

HRID 333831ノート

反応式

HRID 333831 の反応式
[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

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 23925Iron触媒HCID 702Ethanol溶媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

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+].

後処理

  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

出典と根拠

ORDレコード
ord-4455f5f37b494753ae403c4a4a44558f
出典データセット
uspto-grants-2014_11
特許番号
US08883786B2

反応ノート

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