Methyl 2-(2-benzyloxy-4-fluorophenyl)-3-methyl-5-nitrobenzoate → Methyl 5-amino-2-(4-fluoro-2-hydroxyphenyl)-3-methylbenzoate

HRID 909303Notes

Reaction equation

HRID 909303 reaction equation
C([O:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[C:16]1[C:25]([CH3:26])=[CH:24][C:23]([N+:27]([O-])=O)=[CH:22][C:17]=1[C:18]([O:20][CH3:21])=[O:19])C1C=CC=CC=1>CO.O1CCCC1.[Pd]>[NH2:27][C:23]1[CH:24]=[C:25]([CH3:26])[C:16]([C:10]2[CH:11]=[CH:12][C:13]([F:15])=[CH:14][C:9]=2[OH:8])=[C:17]([CH:22]=1)[C:18]([O:20][CH3:21])=[O:19]

Participants

5

Reactant 1

HCID 58026740Methyl 2-(2-benzyloxy-4-fluorophenyl)-3-methyl-5-nitrobenzoate

Product 1

HCID 58027000Methyl 5-amino-2-(4-fluoro-2-hydroxyphenyl)-3-methylbenzoateYield 64%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-(2-benzyloxy-4-fluorophenyl)-3-methyl-5-nitrobenzoate (Reference Compound No. 1-4-(4), 10.7 g, 27.0 mmol) was dissolved in a mixture of methanol (50 mL) and tetrahydrofuran (50 mL), then 10% palladium on charcoal (1.00 g) was added thereto, and then the reaction mixture was stirred under hydrogen atmosphere (3 kgf/cm2) at room temperature for 3 days. After the mixture was filtered, the solvent was removed under reduced pressure. Ethyl acetate was added to the obtained residue, and then filtered to give the titled reference compound (4.79 g) as a pale gray solid. (Yield 64%)

Workup

  1. filtrationAfter the mixture was filtered
  2. customthe solvent was removed under reduced pressure
  3. additionEthyl acetate was added to the obtained residue
  4. filtrationfiltered

Sources & evidence

ORD record
ord-1e6e7482865d4fd39ea55592fedd1449
Source dataset
uspto-grants-2011_09
Patent number
US08017775B2

Reaction notes

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