Tert-butyl (3-methoxy-4-nitrophenyl)acetate → HCID 22244730, compound

HRID 891041Notes

Reaction equation

HRID 891041 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:6]=[CH:7][C:8]=1[N+:9]([O-])=O>C(OCC)(=O)C.CO.[Pd]>[NH2:9][C:8]1[CH:7]=[CH:6][C:5]([CH2:12][C:13]([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:14])=[CH:4][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 1

HCID 22244737Tert-butyl (3-methoxy-4-nitrophenyl)acetate

Product 1

HCID 22244730HCID 22244730, compoundYield 96.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of t-butyl 3-methoxy-4-nitrophenylacetate (0.144 g, 0.539 mmol) and 10% Pd on carbon (0.155 g) in ethyl acetate (8 mL) and methanol (2 mL) was stirred under H2 (40–60 psi) for 2 h. The mixture was filtered through Celite and the filtrate concentrated to afford t-butyl 4-amino-3-methoxyphenylacetate (0.123 g, 96%) as a light yellow oil: 1H NMR (CDCl3, 300 MHz, ppm) 6.70 (m, 3H), 4.04 (bs, 2H), 3.84 (s, 3H), 3.42 (s, 2H), 1.43 (s, 9H).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-d242db47459346888d9e81c7b4301e3f
Source dataset
uspto-grants-2006_02
Patent number
US07001921B1

Reaction notes

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