9-Acetyl-8-hydroxy-1,2-dihydro-6-(3-dimethylaminopropyl)-cyclopenta[c]carbazole-3-one → 1-(6-Acetyl-9H-carbazol-3-yl)-ethanone

HRID 1615048Notes

Reaction equation

HRID 1615048 reaction equation
[C:1]([C:4]1[C:16](O)=[CH:15][C:14]2[N:13](CCCN(C)C)[C:12]3[CH:11]=[CH:10][C:9]4[C:24](=[O:27])[CH2:25]C[C:8]=4[C:7]=3[C:6]=2[CH:5]=1)(=[O:3])[CH3:2]>O.Cl.C(O)C>[C:1]([C:4]1[CH:16]=[CH:15][C:14]2[NH:13][C:12]3[C:7]([C:6]=2[CH:5]=1)=[CH:8][C:9]([C:24](=[O:27])[CH3:25])=[CH:10][CH:11]=3)(=[O:3])[CH3:2]

Participants

5

Reactant 1

HCID 445191329-Acetyl-8-hydroxy-1,2-dihydro-6-(3-dimethylaminopropyl)-cyclopenta[c]carbazole-3-one

Product 1

HCID 2364861-(6-Acetyl-9H-carbazol-3-yl)-ethanoneYield 157.1%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

9-Acetyl-8-hydroxy-1,2-dihydro-6-(3-dimethylaminopropyl)-cyclopenta[c]carbazole-3-one (7.81 g, 21.46 mmol, 1 eq) was dissolved in a mixture of water (20 mL) and 10% HCl solution (20 mL) in ethanol (200 mL), and the homogeneous solution evaporated to dryness. The residue was dried in vacuum overnight to give 8.47 g of Example 4 as a gray solid.

Workup

  1. customthe homogeneous solution evaporated to dryness
  2. customThe residue was dried in vacuum overnight

Sources & evidence

ORD record
ord-123b70d19961416883bb19291363e100
Source dataset
uspto-grants-2014_07
Patent number
US08765738B2

Reaction notes

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