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

HRID 1257179Notes

Reaction equation

HRID 1257179 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

A solution of ethyl 2-(4-fluoro-2-methyl-5-nitrophenyl)acetate (16.79 g, 69.6 mmol) in EtOH (60 mL) was treated with 10% Pd/C (50% wet, 7.41 g, 3.48 mmol) and hydrogenated (3.5 atm) for 2 h. The solids were removed via filtration through diatomaceous earth, rinsed with EtOH and the filtrate was concentrated 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, 1H), 6.59 (d, J=9.6 Hz, 1H), 4.86 (s, 2H), 4.05 (q, J=7.2 Hz, 2H), 3.46 (s, 2H), 2.05 (s, 3H), 1.17 (t, J=7.2 Hz, 3H); MS (ESI) m/z: 212.2 (M+H)+.

Workup

  1. customThe solids were removed via filtration through diatomaceous earth
  2. washrinsed with EtOH
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-1ba6e86542fa40e3a8f34358196d6ed1
Source dataset
uspto-grants-2013_06
Patent number
US08461179B1

Reaction notes

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