Potassium Carbonate → (9H-Carbazol-4-yloxy)acetonitrile

HRID 1057651Notes

Reaction equation

HRID 1057651 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[C:4]([OH:14])=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:22][C:23]#[N:24]>C(#N)C>[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[C:4]([O:14][CH2:22][C:23]#[N:24])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 1042514-Hydroxycarbazole

Product 1

HCID 18671668(9H-Carbazol-4-yloxy)acetonitrileYield 85%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 9H-carbazol-4-ol (1.1 g, 6.0 mmol) in acetonitrile (100 mL) is added potassium carbonate (1.66 g, 12 mmol) and bromoacetonitrile (0.42 mL, 6.0 mmol). The mixture is stirred at room temperature for 20 h. The mixture is partitioned between water and CH2Cl2. The layers are separated and the organic layer dried over anhydrous sodium sulfate, filtered and concentrated. Column chromatography, silica gel (100 mL), using CH2Cl2 as eluent gave 1.13 g (85%) of the title compound; 1H NMR (DMSO-d6) δ5.4, 6.81, 7.18, 7.36, 7.46, 8.09; Anal. Calcd for C14H10N2O: C, 75.66; H, 4.53; N, 12.60. Found: C, 75.18; H, 4.56; N, 12.54.

Workup

  1. customThe mixture is partitioned between water and CH2Cl2
  2. customThe layers are separated
  3. dry with materialthe organic layer dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-87edf34fdb684b83892f85548bb67d73
Source dataset
uspto-grants-2003_02
Patent number
US06514968B1

Reaction notes

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