Toluene → HCID 19018642, compound

HRID 1110025Notes

Reaction equation

HRID 1110025 reaction equation
[C-]#[N:2].[Na+].Br[CH2:5][CH2:6][C:7]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:8]=1[CH3:19].[C:20]1([CH3:26])C=CC=CC=1>O>[C:20]([CH2:26][CH2:5][CH2:6][C:7]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:8]=1[CH3:19])#[N:2]

Participants

5

Reactant 3

HCID 1140TolueneHCID 8929Sodium CyanideHCID 10378814HCID 10378814, compound

Product 1

HCID 19018642HCID 19018642, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2.96 g of sodium cyanide in 60 ml of water was added to a solution of 14 g of 1-(2-bromoethyl)-5,6-dihydro-2-methyl-4H-pyrrolo[3,2,1-ij]quinoline in 100 ml of toluene, and the reaction mixture was heated under reflux for 4 hours. To work up the reaction mixture it was concentrated to dryness, and the residue was washed with water and extracted with dichloromethane. The dichloromethane phase was separated, dried and evaporated. 10.5 g of crude 1-(3-cyanopropyl)-5,6-dihydro-2-methyl-4H-pyrrolo[3,2,1-ij]-quinoline were obtained as a brownish oil.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 4 hours
  3. concentrationwas concentrated to dryness
  4. washthe residue was washed with water
  5. extractionextracted with dichloromethane
  6. customThe dichloromethane phase was separated
  7. customdried
  8. customevaporated

Sources & evidence

ORD record
ord-0d1b4c443bf9411c8372ad25fa94ed1b
Source dataset
uspto-grants-1994_06
Patent number
US05324725

Reaction notes

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