1-(Bromoacetyl)-1,2,3,4-tetrahydroquinoline → 5,6-Dihydro-4H-pyrrolo[3,2,1-ij]quinolin-2(1H)-one

HRID 597706Notes

Reaction equation

HRID 597706 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].Br[CH2:6][C:7]([N:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11][CH2:10]1)=[O:8]>O>[CH2:6]1[C:17]2=[C:18]3[C:13](=[CH:14][CH:15]=[CH:16]2)[CH2:12][CH2:11][CH2:10][N:9]3[C:7]1=[O:8]

Participants

4

Reactant 2

HCID 5838141-(Bromoacetyl)-1,2,3,4-tetrahydroquinolineHCID 6451240Aluminum(III) Chloride

Product 1

HCID 149184935,6-Dihydro-4H-pyrrolo[3,2,1-ij]quinolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
200 °C

Procedure

To a flask containing 30 g. of aluminum chloride is added 20.5 g. of 1-(bromoacetyl)-1,2,3,4-tetrahydroquinoline. After a vigorous initial reaction, the mixture is heated to 200° C. After 30 minutes, the reaction mixture is poured on cold water and the resulting oil is extracted with methylene chloride, dried, and the solvent removed under reduced pressure. The resultant oil is dissolved in ether, the solution cooled and the precipitate sublimed to yield 1,2,5,6-tetrahydro-4H-pyrrolo-(3,2,1-ij)quinolin-2-one, m.p. 90°-93° C.

Workup

  1. additionTo a flask containing 30 g
  2. customAfter a vigorous initial reaction
  3. extractionthe resulting oil is extracted with methylene chloride
  4. customdried
  5. customthe solvent removed under reduced pressure
  6. dissolutionThe resultant oil is dissolved in ether
  7. temperaturethe solution cooled

Sources & evidence

ORD record
ord-63d37c1c4e094998a15253534f1ef93c
Source dataset
uspto-grants-1977_03
Patent number
US04015005

Reaction notes

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