HCID 68984517, compound → HCID 68985805, compound

HRID 1430472Notes

Reaction equation

HRID 1430472 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 (30 psi) at RT for 12 h. The catalyst was filtered off and the filtrate was evaporated. 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, 1H), 6.70 (t, J=7.8 Hz, 1H), 4.50 (s, 2H), 4.06 (m, 2H), 3.53 (s, 2H), 1.16 (t, J=6.9 Hz, 3H); MS (ESI) m/z: 216.2 [M+H]+.

Workup

  1. customat RT
  2. customfor 12 h
  3. filtrationThe catalyst was filtered off
  4. customthe filtrate was evaporated
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-10e29be4ab21430ea26147dbafe3ef68
Source dataset
uspto-grants-2015_01
Patent number
US08940756B2

Reaction notes

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