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Tert-butyl (3-methoxy-4-nitrophenyl)acetate → Tert-butyl 4-amino-3-methoxyphenylacetate

HRID 381249
Notes
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Reaction equation

HRID 381249 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 1

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

Product 1

HCID 22244730Tert-butyl 4-amino-3-methoxyphenylacetateYield 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-06728239e8784035b81423449b7e1e29
Source dataset
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06306840B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes