1,3-Diethyl 2-(3-fluoro-4-nitrophenyl)-2-methylpropanedioate → Diethyl (4-amino-3-fluorophenyl)methylmalonate

HRID 2285805Notes

Reaction equation

HRID 2285805 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:11]([CH3:22])([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O.[H][H]>C(OCC)(=O)C.[Pd]>[NH2:8][C:7]1[CH:6]=[CH:5][C:4]([C:11]([CH3:22])([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:3][C:2]=1[F:1]

Participants

5

Reactant 2

HCID 42638641,3-Diethyl 2-(3-fluoro-4-nitrophenyl)-2-methylpropanedioateHCID 178418361HCID 178418361, compound

Product 1

HCID 11630571Diethyl (4-amino-3-fluorophenyl)methylmalonate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 41.6 g diethyl 2-(4-nitro-3-fluorophenyl)-2-methylmalonate III in 210 ml ethyl acetate in a 500-ml Parr hydrogenation bottle is added 830 mg (2 wt %) of 5% palladium/carbon. The mixture is hydrogenated in a Parr apparatus at 25° C. under 10-12 psi hydrogen for 2.5 hours. The catalyst is removed by filtration through diatomaceous earth (Celite®) and is washed with a few ml of ethyl acetate. The solvent is removed in vacuo to give diethyl 2-(4-amino-3-fluorophenyl)-2-methylmalonate as a viscous oil, 37.6 g [100% wt. yield]. This material is used without purification.

Workup

  1. customThe catalyst is removed by filtration through diatomaceous earth (Celite®)
  2. washis washed with a few ml of ethyl acetate
  3. customThe solvent is removed in vacuo
  4. customto give

Sources & evidence

ORD record
ord-6e726aa6dfd14ec1bdd9724984b2f8c0
Source dataset
uspto-grants-1982_04
Patent number
US04324904

Reaction notes

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