HCID 13265131, compound → HCID 22105824, compound

HRID 1640004Notes

Reaction equation

HRID 1640004 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH3:18])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:6][CH:5]=1)([O-])=O>[Pd].C(O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH:10]([CH3:18])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 13265131HCID 13265131, compound

Product 1

HCID 22105824HCID 22105824, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of tert-butyl 2-(4-nitrophenyl)propanoate (14.4 g, 57.3 mmol) and 10% palladium on carbon (1.44 g, 10% by weight) in ethanol (150 mL) was shaken under an atmosphere of hydrogen at 40 psi for 2 h. After this time, the reaction was filtered through diatomaceous earth, and concentrated under reduced pressure to afford tert-butyl 2-(4-aminophenyl)propanoate (12.5 g, 99%) as an orange oil: 1H NNR (300 MHz, CDCl3) δ 7.07 (d, J=9.1 Hz, 2H), 6.63 (d, J=9.1 Hz, 2H), 3.60 (s, 2H), 3.49 (q, J=7.1 Hz, 1H), 1.40 (d, 3H), 1.38 (s, 9H); ESI MS m/z 222 [M+H]+.

Workup

  1. filtrationAfter this time, the reaction was filtered through diatomaceous earth
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b45dc8b6cb6746eb9113f54c62be5560
Source dataset
uspto-grants-2012_02
Patent number
US08110681B2

Reaction notes

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