Dimethylformamide → 9H-carbazole-9-hexanol

HRID 1876629Notes

Reaction equation

HRID 1876629 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.CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][OH:32]>C(OCC)(=O)C>[CH:10]1[C:11]2[N:12]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][OH:32])[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6854CarbazoleHCID 11430Potassium CarbonateHCID 748286-Chloro-1-hexanol

Product 1

HCID 6402679H-carbazole-9-hexanol

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

To a 500 ml three-neck round bottom flask was added 25 g. carbazole, 218 g. dimethyl formamide, 45.5 g. potassium carbonate and 43 g. 6-chloro-1-hexanol. The reaction mixture was heated at 150° C. for 6 hours, and cooled to room temperature. 500 g. ethyl acetate was added, washed with 250 g water, then 250 g water with 50 g concentrated HCl, then 250 g. saturated brine. The solvent was removed on a rotary evaporator to yield 58 g of a brown semi-solid. The crude product was purified using a silica gel flash chromatography column with dichloromethane as the elutant. The concentrated product fractions yielded 33.3 g. of a white solid product; ˜90% pure by gas chromatography.

Workup

  1. additionTo a 500 ml three-neck round bottom flask was added 25 g
  2. temperaturecooled to room temperature
  3. washwashed with 250 g water
  4. customThe solvent was removed on a rotary evaporator

Sources & evidence

ORD record
ord-b6607d49ba1b48808e3f6a49102fd613
Source dataset
uspto-grants-2012_11
Patent number
US08309650B2

Reaction notes

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