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

HRID 842967Notes

Reaction equation

HRID 842967 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-6f7cdc1f32224243a66c72b835d63f85
Source dataset
uspto-grants-2002_04
Patent number
US06376538B1

Reaction notes

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