Acetyl chloride → 9-Acetyl-8-methoxy-1,2-dihydro-6H-cyclopenta[c]carbazole-3-one

HRID 514795Notes

Reaction equation

HRID 514795 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:7]3[C:8]4[CH2:18][CH2:17][C:16](=[O:19])[C:9]=4[CH:10]=[CH:11][C:12]=3[NH:13][C:14]=2[CH:15]=1.[Al+3].[Cl-].[Cl-].[Cl-].[C:24](Cl)([CH3:26])=[O:25]>ClCCl>[C:24]([C:4]1[C:3]([O:2][CH3:1])=[CH:15][C:14]2[NH:13][C:12]3[CH:11]=[CH:10][C:9]4[C:16](=[O:19])[CH2:17][CH2:18][C:8]=4[C:7]=3[C:6]=2[CH:5]=1)(=[O:25])[CH3:26]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 709006108-Methoxy-1,6-dihydrocyclopenta[c]carbazol-3(2H)-one

Product 1

HCID 711790429-Acetyl-8-methoxy-1,2-dihydro-6H-cyclopenta[c]carbazole-3-oneYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

8-Methoxy-1,2-dihydro-6H-cyclopenta[c]carbazole-3-one (82) (27.8 g, 110.8 mmol, 1 eq) was dissolved in dry dichloromethane (300 mL). Anhydrous AlCl3 (29.5 g, 221.5 mmol, 2 eq) was added in portions with stirring and cooling, followed by the dropwise addition of AcCl (24 mL, 332.4 mmol, 3 eq). The reaction mixture was stirred at about 5° C. for 24 h and poured into ice water (violent foaming should be avoided). The precipitated orange solid was filtered off, washed with water (10×100 mL), CH2Cl2 (3×50 mL), acetone (3×50 mL) to give 26 g (80%) of 9-acetyl-8-methoxy-1,2-dihydro-6H-cyclopenta[c]carbazole-3-one (83).

Workup

  1. temperaturecooling
  2. stirringThe reaction mixture was stirred at about 5° C. for 24 h
  3. filtrationThe precipitated orange solid was filtered off
  4. washwashed with water (10×100 mL), CH2Cl2 (3×50 mL), acetone (3×50 mL)

Sources & evidence

ORD record
ord-0d13a2ec2cc84ed3be24ca1a8ea1e5bc
Source dataset
uspto-grants-2015_08
Patent number
US09108916B2

Reaction notes

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