1-Oxo-1,2-dihydronaphtho[1,8-cd]azepine-3-carboxylic Acid Methyl Ester → 1-Oxo-1,2,3,4-tetrahydronaphtho[1,8-cd]azepine-3-carboxylic Acid Methyl Ester

HRID 660581Notes

Reaction equation

HRID 660581 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH2:6][C:7](=[O:19])[C:8]2[C:13]3[C:14]=1[CH:15]=[N:16][CH:17]=[CH:18][C:12]=3[CH:11]=[CH:10][CH:9]=2)=[O:4]>CCOC(C)=O.[Pd]>[CH3:1][O:2][C:3]([CH:5]1[C:14]2[CH2:15][N:16]=[CH:17][CH:18]=[C:12]3[C:13]=2[C:8](=[CH:9][CH:10]=[CH:11]3)[C:7](=[O:19])[CH2:6]1)=[O:4]

Participants

4

Reactant 1

HCID 688392931-Oxo-1,2-dihydronaphtho[1,8-cd]azepine-3-carboxylic Acid Methyl Ester

Product 1

HCID 866325801-Oxo-1,2,3,4-tetrahydronaphtho[1,8-cd]azepine-3-carboxylic Acid Methyl Ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-oxo-1,2-dihydronaphtho[1,8-cd]azepine-3-carboxylic acid methyl ester (129 mg, 0.5 mmol) in EtOAc (5 mL) is hydrogenated at 1 atm over 10% Pd/C (35 mg) for 18 h. The catalyst is filtered, the solvent is removed under reduced pressure and the residue purified by flash chromatography using a gradient of 0-50% EtOAc/hexane as eluent to give the title compound.

Workup

  1. filtrationThe catalyst is filtered
  2. customthe solvent is removed under reduced pressure
  3. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-4dadfc1b7bd44baca5ef06904656f690
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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