Methanol → HCID 67343009, compound

HRID 1673357Notes

Reaction equation

HRID 1673357 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, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

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

Workup

  1. customAfter insoluble were removed by filtration
  2. customthe solvent was evaporated under reduced pressure
  3. addition11 mL of acetic acid, 11 mL of methanol and 0.33 g of 10% palladium-carbon were added to the obtained residue sequentially
  4. stirringstirred under hydrogen atmosphere at room temperature for 2 hours
  5. customAfter insoluble were removed by filtration
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-ffff1ada6a6b4312b6c9e2bd7d4d2fe9
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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