1,3-Dibromopropane → HCID 15023408, compound

HRID 1089742Notes

Reaction equation

HRID 1089742 reaction equation
[NH:1]1[C:9]2[C:4]3[C:5](=[CH:10][CH:11]=[CH:12][C:3]=3[C:2]1=[O:13])[CH:6]=[CH:7][CH:8]=2.[H-].[Na+].Br[CH2:17][CH2:18][CH2:19]Br>CN(C)C=O>[CH2:17]([N:1]1[C:9]2[C:4]3[C:5](=[CH:10][CH:11]=[CH:12][C:3]=3[C:2]1=[O:13])[CH:6]=[CH:7][CH:8]=2)[CH2:18][CH2:19][N:1]1[C:9]2[C:4]3[C:5](=[CH:10][CH:11]=[CH:12][C:3]=3[C:2]1=[O:13])[CH:6]=[CH:7][CH:8]=2

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 24758Sodium hydrideHCID 67222benz(cd)indol-2(1H)-one

Product 1

HCID 15023408HCID 15023408, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Thirty four grams of benz[cd]indol-2(1H)-one is added with stirring to 500 ml of dry dimethylformamide. Ten grams of 50% sodium hydride (in oil) is added in portions, the reaction is stirred at room temperature for 1 hour, and then on a steam bath for one hour. A deep red/brown solution results. One hundred twenty grams of 1,3-dibromopropane is added in one portion, the red color disappears and a white suspension appears. The mixture is stirred and heated on a steam bath for 16 hours, concentrated to dryness and the residue dissolved in 250 ml of dichloromethane. The solution is passed through hydrous magnesium silicate and rinsed with 100 ml of dichloromethane; on standing at room temperature crystals formed. The solution is cooled to 0° C., collected and washed with 100 ml of hexane. After numerous fractional crystallizations, 12.6 g of (Bs) 1,1'-(1,3-propanediyl)bisbenz[cd]indol-2(1H)-one, mp. 161°-162° C. and (Bt) 1.4 g of 1-(3 -bromopropyl)benz[cd]indol-2(1H)-one, mp. 74°-76° C., is obtained.

Workup

  1. waiton a steam bath for one hour
  2. customA deep red/brown solution results
  3. stirringThe mixture is stirred
  4. temperatureheated on a steam bath for 16 hours
  5. concentrationconcentrated to dryness
  6. dissolutionthe residue dissolved in 250 ml of dichloromethane
  7. washrinsed with 100 ml of dichloromethane
  8. customon standing at room temperature
  9. customformed
  10. temperatureThe solution is cooled to 0° C.
  11. customcollected
  12. washwashed with 100 ml of hexane
  13. customAfter numerous fractional crystallizations, 12.6 g of (Bs) 1,1'-(1,3-propanediyl)bisbenz[cd]indol-2(1H)-one, mp. 161°-162° C. and (Bt) 1.4 g of 1-(3 -bromopropyl)benz[cd]indol-2(1H)-one, mp. 74°-76° C.
  14. customis obtained

Sources & evidence

ORD record
ord-808c90b08d7b4dc28a17da39286448df
Source dataset
uspto-grants-1992_01
Patent number
US05079247

Reaction notes

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