Acetyl chloride → 9-Acetyl-1,2-dihydrocyclopenta[c]carbazol-3(6H)-one

HRID 514788Notes

Reaction equation

HRID 514788 reaction equation
[CH2:1]1[C:16]2[C:15]3[C:14]4[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=4[NH:8][C:7]=3[CH:6]=[CH:5][C:4]=2[C:3](=[O:17])[CH2:2]1.[Al+3].[Cl-].[Cl-].[Cl-].[C:22](Cl)([CH3:24])=[O:23]>C(Cl)Cl>[C:22]([C:12]1[CH:11]=[CH:10][C:9]2[NH:8][C:7]3[CH:6]=[CH:5][C:4]4[C:3](=[O:17])[CH2:2][CH2:1][C:16]=4[C:15]=3[C:14]=2[CH:13]=1)(=[O:23])[CH3:24]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 585448961,6-Dihydrocyclopenta[c]carbazol-3(2H)-one

Product 1

HCID 585448999-Acetyl-1,2-dihydrocyclopenta[c]carbazol-3(6H)-oneYield 56.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,2-dihydro-6H-cyclopenta[c]carbazole-3-one 90 (6 g, 27.1 mmol) was suspended in dry CH2Cl2 (100 mL). Anhydrous AlCl3 (6 g, 45 mmol) was added with stirring on ice bath, followed by the dropwise addition of AcCl (2.4 mL, 33.2 mmol). The reaction mixture was stirred at about 5° C. for 24 h, and poured into ice water. The precipitated grey solid was filtered off, washed with water (2×100 mL), acetone (3×50 mL), diethyl ether (3×50 mL) to give 4 g (56.3%) of 9-acetyl-1,2-dihydro-6H-cyclopenta[c]carbazole-3-one 91.

Workup

  1. stirringThe reaction mixture was stirred at about 5° C. for 24 h
  2. filtrationThe precipitated grey solid was filtered off
  3. washwashed with water (2×100 mL), acetone (3×50 mL), diethyl ether (3×50 mL)

Sources & evidence

ORD record
ord-ada821cfbb8c4f0fb71de56f6b33bea4
Source dataset
uspto-grants-2015_08
Patent number
US09108916B2

Reaction notes

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