Triethylamine → Methyl 3-amino-4-[(tert-butoxycarbonyl)amino]benzoate

HRID 1861862Notes

Reaction equation

HRID 1861862 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]=1[N+:19]([O-])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C>CO.C(OCC)(=O)C.[Pd]>[NH2:19][C:10]1[CH:11]=[C:12]([CH:17]=[CH:18][C:9]=1[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:13]([O:15][CH3:16])=[O:14]

Participants

6

Reactant 2

HCID 8471TriethylamineHCID 22988663Methyl 4-[(tert-butoxy)carbonylamino]-3-nitrobenzoate

Product 1

HCID 18621647Methyl 3-amino-4-[(tert-butoxycarbonyl)amino]benzoateYield 100.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Part 1. To a solution of methyl 4-[(tert-butoxy)carbonylamino]-3-nitrobenzoate (0.44 g, 1.5 mmol) in methanol (2 mL), ethyl acetate (3 mL) and triethylamine (0.21 mL, 1.5 mmol) was added 10% Pd on carbon (159 mg, 0.15 mmol). The reaction mixture was hydrogenated under 1 atm H2 for 3.5 hours, filtered, and concentrated in vacuo to yield methyl 3-amino-4-[(tert-butoxycarbonyl)amino]benzoate (0.40 g, 99%) as a white solid. ES-MS (M+H—C4H8)+=211.1.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6b85ecfab89d4dd0968a8d68073a80f5
Source dataset
uspto-grants-2003_03
Patent number
US06534535B1

Reaction notes

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