HCID 67403053, compound → HCID 22402069, compound

HRID 906111Notes

Reaction equation

HRID 906111 reaction equation
[NH2:1][C:2]([C:4]1[CH:16]=[CH:15][C:7]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[CH:6][C:5]=1[N+:17]([O-])=O)=[O:3]>[Pd].C(OCC)(=O)C>[NH2:17][C:5]1[CH:6]=[C:7]([CH:15]=[CH:16][C:4]=1[C:2]([NH2:1])=[O:3])[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]

Participants

4

Reactant 1

HCID 67403053HCID 67403053, compound

Product 1

HCID 22402069HCID 22402069, compoundYield 95.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1,1-dimethylethyl 4-(aminocarbonyl)-3-nitrobenzoate (213 mg, 0.80 mmol), 10% palladium on charcoal (Degussa type, 200 mg) in ethyl acetate (20 mL) was shaken in a Parr hydrogenation apparatus at 35 psi for 4 hours. The reaction mixture was filtered and concentrated to give 1,1-dimethylethyl 3-amino-4-(aminocarbonyl)benzoate (180 mg, 95% yield). MS (EI) for C12H16N2O3: 237 (MH+).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-523d6bf1bb2843eb8b13e0421aa44763
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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