Hydrochloric Acid → HCID 19372801, compound

HRID 129223Notes

Reaction equation

HRID 129223 reaction equation
[N:1]([CH:4]1[CH2:27][C:8]2=[CH:9][N:10]([S:17]([C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=3)(=[O:19])=[O:18])[C:11]3[CH:12]=[CH:13][C:14]([O:15][CH3:16])=[C:6]([C:7]=32)[C:5]1=[O:28])=[N+]=[N-].C(O)C.[ClH:32]>[C].[Pd]>[ClH:32].[NH2:1][CH:4]1[CH2:27][C:8]2=[CH:9][N:10]([S:17]([C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=3)(=[O:19])=[O:18])[C:11]3[CH:12]=[CH:13][C:14]([O:15][CH3:16])=[C:6]([C:7]=32)[C:5]1=[O:28]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 19029024HCID 19029024, compound

Product 1

HCID 19372801HCID 19372801, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 178418390HCID 178418390, compoundCatalyst

Procedure

To a suspension of 4-azido-3,4-dihydro-6-methoxy-1-p-toluenesulfonylbenz[cd]indol-5(1H)-one (2.0 g, 5.0 mmol) in ethanol (100 mmol) were added conc. hydrochloric acid (2.5 ml) and 10% palladium-carbon (400 mg). The mixture was stirred for 4 hours at room temperature under hydrogen atmosphere of 3 atmospheres pressure. After completion of the reaction, the catalyst was filtered off. The filtrate was subjected to distillation, and the residue was washed with ethyl ether to give 1.6 g (80%) of crude crystals of the title compound.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe catalyst was filtered off
  3. distillationThe filtrate was subjected to distillation
  4. washthe residue was washed with ethyl ether

Sources & evidence

ORD record
ord-4cc126164f774b3daf020878d2e832d0
Source dataset
uspto-grants-1995_11
Patent number
US05466689

Reaction notes

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