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Potassium Carbonate → [(9-Benzyl-6-methoxy-9H-carbazol-4-yl)oxy]acetonitrile

HRID 1057656
Notes
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Reaction equation

HRID 1057656 reaction equation
[CH2:1]([N:8]1[C:20]2[CH:19]=[CH:18][CH:17]=[C:16]([OH:21])[C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[C:12]([O:22][CH3:23])[CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:31][C:32]#[N:33]>CN(C=O)C>[CH2:1]([N:8]1[C:20]2[CH:19]=[CH:18][CH:17]=[C:16]([O:21][CH2:31][C:32]#[N:33])[C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[C:12]([O:22][CH3:23])[CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 97964539-Benzyl-6-methoxy-9H-carbazol-4-ol

Product 1

HCID 18671663[(9-Benzyl-6-methoxy-9H-carbazol-4-yl)oxy]acetonitrileYield 31.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a mixture of 9-benzyl-6-methoxy-9H-carbazol-4-ol (1.21 g, 4.0 mmol) in DMF (25 mL) is added potassium carbonate (2.07 g, 15 mmol) and bromoacetonitrile (0.7 mL) 10 mmol). The mixture is heated at 120° C. overnight. The mixture is partitioned between water and Et2O. The organic layer is washed twice with water (100 mL) and dried over anhydrous sodium sulfate. The residue is dissolved in CH2Cl2 and passed through a silica gel plug. The filtrates are concentrated to dryness to give 0.43 g (31%) of the title compound; IR (drift) 1487, 1469, 1449, 1439, 1291, 1275, 1211, 1181, 1170, 1147, 1120, 775, 745, 705, 697 cm−1. 1H NMR (CDCl3) δ3.94, 5.06, 5.48, 6.7, 7.09, 7.24, 7.36, 7.81; Anal. Calcd for C22H18N2O2: C, 77.17; H, 5.30; N, 8.18. Found: C, 76.68; H, 5.31; N, 8.08.

Workup

  1. customThe mixture is partitioned between water and Et2O
  2. washThe organic layer is washed twice with water (100 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. dissolutionThe residue is dissolved in CH2Cl2
  5. concentrationThe filtrates are concentrated to dryness

Sources & evidence

ORD record
ord-e0ab5ac9644c41169b29ced6e631a766
Source dataset
uspto-grants-2003_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06514968B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes