Methanol → HCID 67343009, compound

HRID 2191640Notes

Reaction equation

HRID 2191640 reaction equation
CO.[Cl:3][C:4]1[CH:5]=[C:6]([C:10]2[CH:22]=[CH:21][C:13]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[C:12]([N+:23]([O-])=O)[CH:11]=2)[CH:7]=[CH:8][CH:9]=1>[C].[Pd].C(OCC)(=O)C>[NH2:23][C:12]1[CH:11]=[C:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([Cl:3])[CH:5]=2)[CH:22]=[CH:21][C:13]=1[C:14]([O:16][C:17]([CH3:19])([CH3:20])[CH3:18])=[O:15]

Participants

5

Reactant 2

HCID 887MethanolHCID 67343762HCID 67343762, compound

Product 1

HCID 67343009HCID 67343009, compoundYield 69.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a mixed solution of methanol 11 mL and ethyl acetate 11 mL of tert-butyl 4-(3-chlorophenyl)-2-nitrobenzoate 1.1 g was added 10% palladium-carbon 0.33 g, and it was stirred under hydrogen atmosphere at room temperature for 3 hours. The solvent was removed under reduced pressure after insoluble matter was filtrated. To the obtained residue, were added acetic acid 11 mL, methanol 11 mL and 10% palladium-carbon 0.33 g sequentially, and it was stirred under hydrogen atmosphere at room temperature for 2 hours. The solvent was removed under reduced pressure after insoluble matter was filtrated to give tert-butyl 2-amino-4-(3-chlorophenyl)benzoate 0.70 g of white solid.

Workup

  1. customThe solvent was removed under reduced pressure after insoluble matter
  2. filtrationwas filtrated
  3. additionTo the obtained residue, were added acetic acid 11 mL, methanol 11 mL and 10% palladium-carbon 0.33 g sequentially
  4. stirringit was stirred under hydrogen atmosphere at room temperature for 2 hours
  5. customThe solvent was removed under reduced pressure after insoluble matter
  6. filtrationwas filtrated

Sources & evidence

ORD record
ord-c46a0486a1224360afe10e4c4ef185b2
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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