Ethyl Acetate → 5-[N-(2-aminobenzoyl)amino]-2-phenyl-1,3,4,5-tetrahydrobenz[cd]indole

HRID 1637271Notes

Reaction equation

HRID 1637271 reaction equation
[N+:1]([C:4]1[CH:30]=[CH:29][CH:28]=[CH:27][C:5]=1[C:6]([NH:8][CH:9]1[C:19]2[C:20]3[C:12](=[C:13]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[NH:14][C:15]=3[CH:16]=[CH:17][CH:18]=2)[CH2:11][CH2:10]1)=[O:7])([O-])=O.C(OCC)(=O)C>CO.[C].[Pd]>[NH2:1][C:4]1[CH:30]=[CH:29][CH:28]=[CH:27][C:5]=1[C:6]([NH:8][CH:9]1[C:19]2[C:20]3[C:12](=[C:13]([C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)[NH:14][C:15]=3[CH:16]=[CH:17][CH:18]=2)[CH2:11][CH2:10]1)=[O:7]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 193481975-[N-(2-nitrobenzoyl)amino]-2-phenyl-1,3,4,5-tetrahydrobenz[cd]indole

Product 1

HCID 193481655-[N-(2-aminobenzoyl)amino]-2-phenyl-1,3,4,5-tetrahydrobenz[cd]indoleYield 58%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A portion (250 mg) of the compound obtained in Example 128 was suspended in methanol (50 ml) and to the suspension was added 10% palladium-carbon (25 mg). The mixture was stirred for 3.5 hours at room temperature under a hydrogen atmosphere. Ethyl acetate was added to the reaction mixture, the catalyst was filtered off and the filtrate was concentrated under reduced pressure. The residue was crystallized from ether to yield 134 mg (58%) of the titled compound.

Workup

  1. filtrationthe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was crystallized from ether

Sources & evidence

ORD record
ord-88b2671a4d614ec0be1c16949da1b05b
Source dataset
uspto-grants-2000_03
Patent number
US06040331

Reaction notes

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