1,2-Dichloroethane → 6-Methoxycarbonyl-2a-(4-bromobutyl)-2a,3,4,5-tetrahydrobenz[cd]-indole-2(1H)-one

HRID 276917Notes

Reaction equation

HRID 276917 reaction equation
ClC(Cl)(O[C:5](=[O:11])[O:6][C:7](Cl)(Cl)Cl)Cl.ClCCCl.[Cl-].[Al+3].[Cl-].[Cl-].[Br:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]12[CH2:37][CH2:36][CH2:35][C:33]3[C:34]1=[C:29]([CH:30]=[CH:31][CH:32]=3)[NH:28][C:27]2=[O:38]>CO>[CH3:7][O:6][C:5]([C:32]1[CH:31]=[CH:30][C:29]2[NH:28][C:27](=[O:38])[C:26]3([CH2:25][CH2:24][CH2:23][CH2:22][Br:21])[CH2:37][CH2:36][CH2:35][C:33]=1[C:34]=23)=[O:11]

Participants

6

Reactant 4

HCID 111,2-Dichloroethane2×HCID 94429TriphosgeneHCID 6451240Aluminum(III) ChlorideHCID 105908942a-(4-Bromobutyl)-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-one

Product 1

HCID 110030546-Methoxycarbonyl-2a-(4-bromobutyl)-2a,3,4,5-tetrahydrobenz[cd]-indole-2(1H)-oneYield 35%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A 1.44 g (4.87 mmol) portion of triphosgene was added to 1,2-dichloroethane suspension (30 ml) of aluminum chloride (1.95 g, 14.61 mmol) and the mixture was cooled to 0° C. Thereto was added 30 ml of 1,2-dichloroethane solution containing 1.50 g (1.64 mmol) of 2a-(4-bromobutyl)-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-one, subsequently carrying out 2 hours of stirring at 0° C. The reaction solution was mixed with 50 ml of methanol, stirred at a room temperature for 1 hour, extracted with chloroform and then washed with 1 N hydrochloric acid. After drying (Na2SO4), the solvent was evaporated under a reduced pressure, and the thus obtained oily substance was purified by a silica gel column chromatography (300 cc; elution with ethyl acetate-hexane=1:1) and then recrystallized from ethyl acetate-hexane to obtain 0.63 g of the title compound (35% in yield).

Workup

  1. stirringstirred at a room temperature for 1 hour
  2. extractionextracted with chloroform
  3. washwashed with 1 N hydrochloric acid
  4. dry with materialAfter drying (Na2SO4)
  5. customthe solvent was evaporated under a reduced pressure
  6. customthe thus obtained oily substance was purified by a silica gel column chromatography (300 cc; elution with ethyl acetate-hexane=1:1)
  7. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-1d9f724e836c4d0bbfc05d81d301d696
Source dataset
uspto-grants-2002_03
Patent number
US06355642B1

Reaction notes

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