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

HRID 2267608Notes

Reaction equation

HRID 2267608 reaction equation
[CH3:1][O:2][C:3](=[O:27])[CH:4]([CH:9]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=1[N+:18]([O-])=O)[C:5]([O:7][CH3:8])=[O:6].[Cl-].[NH4+]>CO.[Zn]>[CH3:1][O:2][C:3](=[O:27])[CH:4]([CH:9]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=1[NH2:18])[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d9834246cdae46b48dcaf50ca013b2e7
Source dataset
uspto-grants-2010_12
Patent number
US07858776B2

Reaction notes

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