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

HRID 1615010Notes

Reaction equation

HRID 1615010 reaction equation
[CH3:1][N:2]([CH3:25])[CH2:3][CH2:4][CH2:5][N:6]1[C:18]2[CH:17]=[CH:16][C:15]3[C:19](=[O:22])[CH2:20][CH2:21][C:14]=3[C:13]=2[C:12]2[CH:11]=[CH:10][C:9]([O:23][CH3:24])=[CH:8][C:7]1=2.[Al+3].[Cl-].[Cl-].[Cl-].[C:30](Cl)([CH3:32])=[O:31].C([O-])([O-])=O.[Na+].[Na+]>C1([N+]([O-])=O)C=CC=CC=1.O>[C:30]([C:10]1[C:9]([O:23][CH3:24])=[CH:8][C:7]2[N:6]([CH2:5][CH2:4][CH2:3][N:2]([CH3:1])[CH3:25])[C:18]3[CH:17]=[CH:16][C:15]4[C:19](=[O:22])[CH2:20][CH2:21][C:14]=4[C:13]=3[C:12]=2[CH:11]=1)(=[O:31])[CH3:32]

Participants

7

Reactant 4

HCID 6367Acetyl chlorideHCID 10340Sodium CarbonateHCID 6451240Aluminum(III) ChlorideHCID 585449126-[3-(Dimethylamino)propyl]-8-methoxy-1,6-dihydrocyclopenta[c]carbazol-3(2H)-one

Product 1

HCID 453808019-Acetyl-8-methoxy-1,2-dihydro-6-(3-dimethylaminopropyl)-cyclopenta[c]carbazole-3-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7416NitrobenzeneSolvent

Procedure

A solution of compound 37 (0.84 g, 2.51 mmol) in PhNO2 (20 mL) was cooled in an ice bath. Then AlCl3 (1.7 g, 12.7 mmol, 5 eq.) and after that, AcCl (0.9 mL, 12.7 mmol, 5 eq.) were added. The mixture was kept for 40 min (LC/MS monitoring), diluted with water, neutralized with Na2CO3, extracted with CHCl3, and evaporated. The product was purified on a short thick column, eluent: CHCl3-MeOH 99:1→90:10. Yield of 38: 0.658 g (69%).

Workup

  1. extractionextracted with CHCl3
  2. customevaporated
  3. customThe product was purified on a short thick column, eluent

Sources & evidence

ORD record
ord-8637bab3eea6421d9b86662c97046bba
Source dataset
uspto-grants-2014_07
Patent number
US08765738B2

Reaction notes

Loading…