HCID 69034741, compound → Methyl 2-amino-4-[(tert-butoxycarbonyl)amino]benzoate

HRID 2215864Notes

Reaction equation

HRID 2215864 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:6][C:5]=1[N+:18]([O-])=O>C(OCC)(=O)C.[Pd]>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([O:13][C:14]([CH3:15])([CH3:17])[CH3:16])=[O:12])=[CH:6][C:5]=1[NH2:18]

Participants

4

Reactant 1

HCID 69034741HCID 69034741, compound

Product 1

HCID 21056495Methyl 2-amino-4-[(tert-butoxycarbonyl)amino]benzoateYield 100.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(tert-butoxycarbonylamino)-2-nitro-benzoic acid methyl ester (7.0 g, 23.6 mmoles) in 400 mL ethyl acetate was added 1.0 g 10% Pd/C. The reaction mixture was subjected to hydrogenation using a balloon for 24–36 hrs or until the reaction was complete as monitored by HPLC. The mixture was filtered through a celite bed, and the solid cake was thoroughly washed by ethyl acetate. The filtrate was concentrated in vacuo to dryness to afford the title compound (6.3 g, 99%). ES+ MS showed 267 m/z, the correct mass for the product.

Workup

  1. customfor 24–36 hrs
  2. filtrationThe mixture was filtered through a celite bed
  3. washthe solid cake was thoroughly washed by ethyl acetate
  4. concentrationThe filtrate was concentrated in vacuo to dryness

Sources & evidence

ORD record
ord-f0a9c4e1cd384922952fe2a7b0854bf4
Source dataset
uspto-grants-2006_09
Patent number
US07109332B2

Reaction notes

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