HCID 53420017, compound → 1215074-48-8

HRID 62740Notes

Reaction equation

HRID 62740 reaction equation
[CH3:1][O:2][C:3]1[CH:15]=[C:14]([N+:16]([O-])=O)[CH:13]=[CH:12][C:4]=1[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6]>CO.[Pd]>[NH2:16][C:14]1[CH:13]=[CH:12][C:4]([C:5]([O:7][C:8]([CH3:10])([CH3:11])[CH3:9])=[O:6])=[C:3]([O:2][CH3:1])[CH:15]=1

Participants

4

Reactant 1

HCID 53420017HCID 53420017, compound

Product 1

HCID 593777671215074-48-8Yield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

tert-Butyl 2-methoxy-4-nitrobenzoate (2) (271 mg, 1.07 mmol) was dissolved in MeOH (270 mL) and passed through a Thales ‘H-cube’ cartridge (10% Pd/C) at a flow rate of 1 mL/min at 25° C. under full H2 mode. The solvent was removed in vacuo to afford tert-butyl 4-amino-2-methoxybenzoate (3) (234 mg, 92%) as a pale yellow solid: m/z 222 [M−H]− (ES−); 1H-NMR (400 MHz, DMSO-d6) δ: 7.41 (1H, d), 6.16 (1H, d), 6.09 (1H, dd), 5.82 (2H, br s), 3.68 (3H, s), 1.45 (9H, s).

Workup

  1. customat 25° C.
  2. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-e1cec93805c948b6bc8289e6761533fe
Source dataset
uspto-grants-2016_09
Patent number
US09447028B2

Reaction notes

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