Ammonium Chloride → Dimethyl [2-(2-amino-4-fluorophenyl)-1-phenylethyl]malonate

HRID 1593275ノート

反応式

HRID 1593275 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([CH:16]([C:21]([O:23][CH3:24])=[O:22])[C:17]([O:19][CH3:20])=[O:18])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:4]([N+:25]([O-])=O)[CH:3]=1.[Cl-].[NH4+]>CO.[Zn]>[NH2:25][C:4]1[CH:3]=[C:2]([F:1])[CH:7]=[CH:6][C:5]=1[CH2:8][CH:9]([CH:16]([C:21]([O:23][CH3:24])=[O:22])[C:17]([O:19][CH3:20])=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

参加物

5

反応物 2

HCID 25517Ammonium ChlorideHCID 59688514Dimethyl [2-(4-fluoro-2-nitrophenyl)-1-phenylethyl]malonate

生成物 1

HCID 58997962Dimethyl [2-(2-amino-4-fluorophenyl)-1-phenylethyl]malonate収率 90%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 887Methanol溶媒

実験手順

To a solution of dimethyl [2-(4-fluoro-2-nitrophenyl)-1-phenylethyl]malonate (8a) (5.0 g) in methanol (20 mL) was added ammonium chloride (1.5 g) and zinc dust (11.0 g). The reaction mixture was then heated to reflux for 1 h. The reaction mixture was filtered through a diatomaceous earth pad, and the organic solvents were removed in vacuo. The resulting yellow oil was dissolved in ethyl acetate (100 mL) and washed with saturated aqueous potassium carbonate solution (2×), the organic layer was dried, filtered, and concentrated in vacuo to afford the title compound as a tan gum (4.1 g, 90%). MS APCI, m/z=346 (M+1). LC/MS: 2.51 min.

後処理

  1. temperatureThe reaction mixture was then heated
  2. temperatureto reflux for 1 h
  3. filtrationThe reaction mixture was filtered through a diatomaceous earth pad
  4. customthe organic solvents were removed in vacuo
  5. dissolutionThe resulting yellow oil was dissolved in ethyl acetate (100 mL)
  6. washwashed with saturated aqueous potassium carbonate solution (2×)
  7. customthe organic layer was dried
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-55277b36391f48bf94dbf7ee214f7f3c
出典データセット
uspto-grants-2007_11
特許番号
US07294622B2

反応ノート

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