Indoline → HCID 13324749, compound

HRID 371491Notes

Reaction equation

HRID 371491 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4]1.F[C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[C:16]#[N:17]>CS(C)=O>[N:3]1([C:13]2[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=2)[C:16]#[N:17])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 10328IndolineHCID 24758Sodium hydrideHCID 678803-Fluorobenzonitrile

Product 1

HCID 13324749HCID 13324749, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

4.63 g (0.0193 mole, 1.1 equiv.) 99% NaH was added in one portion to a stirred solution of 19.8 ml (0.175 mole) indoline in 90 ml sieve dried DMSO under nitrogen at room temperature. After 65 minutes, the mixture was cooled in an ice bath and treated dropwise with a solution of 23.43 g (0.193 mole, 1.1 equiv.) 3-fluorobenzonitrile in 34 ml dry DMSO. The product was permitted to stir overnight at room temperature, poured onto 300 ml ice and extracted with CHCl3. The organic layer was washed five times with water (800 ml portions), dried over MgSO4, and concentrated to give 42.75 g (38.6 g theory) of oil. 2.0 g of the crude product was chromatographed on silica gel (104 g) using ether-hexane thus affording a 0.99 g sample of an oil of pure 3-(1-indolinyl)benzonitrile.

Workup

  1. temperaturethe mixture was cooled in an ice bath
  2. extractionextracted with CHCl3
  3. washThe organic layer was washed five times with water (800 ml portions)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customto give 42.75 g (38.6 g theory) of oil
  7. custom2.0 g of the crude product was chromatographed on silica gel (104 g)

Sources & evidence

ORD record
ord-23457b09ec7d459b9f0c653c55b57499
Source dataset
uspto-grants-1985_07
Patent number
US04532333

Reaction notes

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