Potassium Carbonate → 9-Acetyl-8-hydroxy-1,2-dihydro-6-(3-dimethylaminopropyl)-cyclopenta[c]carbazole-3-one

HRID 514797Notes

Reaction equation

HRID 514797 reaction equation
[C:1]([C:4]1[C:16]([O:17]C)=[CH:15][C:14]2[N:13]([CH2:19][CH2:20][CH2:21][N:22]([CH3:24])[CH3:23])[C:12]3[CH:11]=[CH:10][C:9]4[C:25](=[O:28])[CH2:26][CH2:27][C:8]=4[C:7]=3[C:6]=2[CH:5]=1)(=[O:3])[CH3:2].Cl.N1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>CN1C(=O)CCC1>[C:1]([C:4]1[C:16]([OH:17])=[CH:15][C:14]2[N:13]([CH2:19][CH2:20][CH2:21][N:22]([CH3:23])[CH3:24])[C:12]3[CH:11]=[CH:10][C:9]4[C:25](=[O:28])[CH2:26][CH2:27][C:8]=4[C:7]=3[C:6]=2[CH:5]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 10176127Pyridinium chlorideHCID 453808019-Acetyl-8-methoxy-1,2-dihydro-6-(3-dimethylaminopropyl)-cyclopenta[c]carbazole-3-one

Product 1

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

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 9-acetyl-8-methoxy-1,2-dihydro-6-(3-dimethylaminopropyl)-cyclopenta[c]carbazole-3-one (84) (22 g, 58.2 mmol, 1 eq) and pyridine hydrochloride (134.4 g, 1164 mmol, 20 eq) in NMP (150 mL) was refluxed for 10 h. The reaction mixture was cooled to room temperature and poured into the 10% aqueous K2CO3 solution (3 L). The precipitated dark green solid was filtered off, washed with water (5×100 mL) and dried. The crude product was purified by column chromatography (eluent 10%-20% MeOH in EtOAc) to give 7.81 (37%) of pure 9-acetyl-8-hydroxy-1,2-dihydro-6-(3-dimethylaminopropyl)-cyclopenta[c]carbazole-3-one as a pale yellow solid.

Workup

  1. filtrationThe precipitated dark green solid was filtered off
  2. washwashed with water (5×100 mL)
  3. customdried
  4. customThe crude product was purified by column chromatography (eluent 10%-20% MeOH in EtOAc)

Sources & evidence

ORD record
ord-d486c71a1fa3478e9457379140a33c1a
Source dataset
uspto-grants-2015_08
Patent number
US09108916B2

Reaction notes

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