Methanol → 9-Allylcarbazole

HRID 2106973Notes

Reaction equation

HRID 2106973 reaction equation
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH2:16](Br)[CH:17]=[CH2:18].CO>CN(C=O)C>[CH2:18]([N:12]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:1][CH:2]=[CH:3][CH:4]=2)[CH:17]=[CH2:16]

Participants

6

Reactant 4

HCID 887MethanolHCID 6854CarbazoleHCID 7841Allyl bromideHCID 24758Sodium hydride3×

Product 1

HCID 30903939-AllylcarbazoleYield 78.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

83.6 g (0.5 mol) of carbazole are dissolved in 250 ml of dry DMF. This solution is added dropwise at 0° C. to a suspension of 12.0 g (0.4 mol) of sodium hydride in 500 ml of DMF. An 80% oil suspension of NaH is used. After stirring for a further 2 hours at 0° C., 38 ml (0.45 mol) of allyl bromide are added dropwise. After the end of the addition, the mixture is warmed to room temperature within one hour, with stirring. To decompose residual NaH, 100 ml of methanol are also added. The solvent mixture is then removed in vacuo in a rotary evaporator and the residue is extracted with 400 ml of petroleum ether (40°-60° C.). Finally, the petroleum ether extract is filtered and evaporated in a rotary evaporator. The remaining brownish oil is distilled in a high vacuum. This gives 65.1 g of a pale yellow, microcrystalline solid. Melting point: 52°-54° C., boiling point: 112° C./13 Pa. Yield 78.5% of theory.

Workup

  1. additionAfter the end of the addition
  2. temperaturethe mixture is warmed to room temperature within one hour
  3. stirringwith stirring
  4. additionare also added
  5. customThe solvent mixture is then removed in vacuo in a rotary evaporator
  6. extractionthe residue is extracted with 400 ml of petroleum ether (40°-60° C.)
  7. extractionFinally, the petroleum ether extract
  8. filtrationis filtered
  9. customevaporated in a rotary evaporator
  10. distillationThe remaining brownish oil is distilled in a high vacuum

Sources & evidence

ORD record
ord-b5264fcf89d84bc3b7441f14d54633e4
Source dataset
uspto-grants-1990_06
Patent number
US04933053

Reaction notes

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