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

HRID 1966275Notes

Reaction equation

HRID 1966275 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-d3d38b88db194eac8058c6e214a15358
Source dataset
uspto-grants-2013_04
Patent number
US08420635B2

Reaction notes

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