HCID 68984517, compound → HCID 68985805, compound

HRID 1930413Notes

Reaction equation

HRID 1930413 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N+:9]([O-])=O)=[CH:4][C:3]=1[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]>CCOC(C)=O.[Pd]>[NH2:9][C:5]1[C:6]([F:8])=[CH:7][C:2]([F:1])=[C:3]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:4]=1

Participants

4

Reactant 1

HCID 68984517HCID 68984517, compound

Product 1

HCID 68985805HCID 68985805, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of ethyl 2-(2,4-difluoro-5-nitrophenyl)acetate (16 g, 130 mmol) and 10% Pd/C (1.6 g, 1.5 mmol) in EtOAc was hydrogenated at 30 psi at RT for 12 h. The catalyst was filtered off and the filtrate was evaporated. Then the residue was purified by column chromatography to give ethyl 2-(5-amino-2,4-difluorophenyl)acetate (14 g, 99% yield). 1H NMR (300 MHz, DMSO-d6): δ 6.98 (t, J=9.9 Hz, 1 H), 6.70 (t, J=7.8 Hz, 1 H), 4.50 (s, 2 H), 4.06 (m, 2 H), 3.53 (s, 2 H), 1.16 (t, 0.7=6.9 Hz, 3 H); MS (ESI) m/z: 216.2 [M+H]+.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThen the residue was purified by column chromatography

Sources & evidence

ORD record
ord-2329dbd0356147f4a45f12456e4634b0
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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