5-(4-Nitrobenzoyl)-6 7-dihydro-5H-dibenz[b,d]azepine → 5-(4-Aminobenzoyl)-6,7-dihydro-5H-dibenz[b,d]azepine

HRID 355846Notes

Reaction equation

HRID 355846 reaction equation
[N+:1]([C:4]1[CH:26]=[CH:25][C:7]([C:8]([N:10]2[CH2:16][CH2:15][C:14]3[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=3[C:12]3[CH:21]=[CH:22][CH:23]=[CH:24][C:11]2=3)=[O:9])=[CH:6][CH:5]=1)([O-])=O.[H][H]>C([O-])(=O)C.[Pd]>[NH2:1][C:4]1[CH:26]=[CH:25][C:7]([C:8]([N:10]2[CH2:16][CH2:15][C:14]3[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=3[C:12]3[CH:21]=[CH:22][CH:23]=[CH:24][C:11]2=3)=[O:9])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 540065545-(4-Nitrobenzoyl)-6 7-dihydro-5H-dibenz[b,d]azepineHCID 178418361HCID 178418361, compound

Product 1

HCID 538444955-(4-Aminobenzoyl)-6,7-dihydro-5H-dibenz[b,d]azepineYield 94.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 175AcetateSolvent

Procedure

A solution of 0.15 g of 5-(4-nitrobenzoyl)-6,7-dihydro-5H-dibenz[b,d]azepine in 20 μl of ethanolethyl acetate and 10 mg of 10% palladium-on-carbon is hydrogenated under 35 pounds per square inch of hydrogen for 8 hr. The mixture is filtered through diatomaceous earth and the filtrate evaporated to give 0.13 g of product as a light yellow solid.

Workup

  1. filtrationThe mixture is filtered through diatomaceous earth
  2. customthe filtrate evaporated

Sources & evidence

ORD record
ord-7ce807c42ba54f25baeb77d38987c273
Source dataset
uspto-grants-1998_11
Patent number
US05834461

Reaction notes

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