Ethyl 2-(4-fluoro-2-methyl-5-nitrophenyl)acetate → Ethyl 2-(5-amino-4-fluoro-2-methylphenyl)acetate

HRID 1930410Notes

Reaction equation

HRID 1930410 reaction equation
[F:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:4]([CH3:17])[CH:3]=1>CCO.[Pd]>[NH2:8][C:7]1[C:2]([F:1])=[CH:3][C:4]([CH3:17])=[C:5]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:6]=1

Participants

4

Reactant 1

HCID 68983461Ethyl 2-(4-fluoro-2-methyl-5-nitrophenyl)acetate

Product 1

HCID 69298814Ethyl 2-(5-amino-4-fluoro-2-methylphenyl)acetateYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Ethyl 2-(4-fluoro-2-methyl-5-nitrophenyl)acetate (16.79 g, 69.6 mmol, 1.00) in EtOH (60 ml) was shaken with 10% Pd/C (50% H2O) (7.41 g, 3.48 mmol, 0.050 eq) under H2 (3.5 atm) at RT for 2 h until H2 uptake was complete. The completed reaction was filtered on Celite, rinsing forward with EtOH. The cake was washed well with EtOH and the combined filtrates were concentrated and pumped on to afford ethyl 2-(5-amino-4-fluoro-2-methylphenyl)acetate (13.18 g, 90% yield) as a brown oil. 1H NMR (400 MHz, DMSO-d6): δ 6.80 (d, J=12.4 Hz, 1 H), 6.59 (d, J=9.6 Hz, 1 H), 4.86 (s, 2 H), 4.05 (q, J=7.2 Hz, 2 H), 3.46 (s, 2 H), 2.05 (s, 3 H), 1.17 (t, J=7.2 Hz, 3 H); MS (ESI) m/z: 212.2 (M+H)+.

Workup

  1. customThe completed reaction
  2. filtrationwas filtered on Celite
  3. washrinsing forward with EtOH
  4. washThe cake was washed well with EtOH
  5. concentrationthe combined filtrates were concentrated

Sources & evidence

ORD record
ord-c8ac081f2ebc4f18aca2fd4073c4bb89
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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