Indoline → HCID 13324709, compound

HRID 371489Notes

Reaction equation

HRID 371489 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:20]=[CH:19][CH:18]=[CH:17][C:14]=1[C:15]#[N:16]>CS(C)=O>[N:3]1([C:19]2[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:20]=2)[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 678552-Fluorobenzonitrile

Product 1

HCID 13324709HCID 13324709, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

4.94 g (0.206 mole) 99% NaH was added in one portion to a solution of 21.6 ml (0.188 mole) indoline in 85 ml sieve dried dimethylsulfoxide (DMSO) at room temperature. The resulting slurry was permitted to stir at room temperature for 2 hours and then cooled in an ice bath. A solution of 25 g (0.206 moles) 2-fluorobenzonitrile in 35 ml DMSO was added dropwise. At the end of the addition, the ice bath was removed and the mixture was permitted to stir at room temperature overnight (about 16 hours). The product was poured onto 300 ml of ice and extracted with CHCl3 (300 ml). The organic phase was thrice washed with water (500 ml portions), brine (500 ml), dried (Na2SO4) and concentrated to give 39.9 g (96.4%) of crude material. Two recrystallizations from isopropyl ether afforded 4-(1-indolinyl)benzonitrile, m.p. 88.5°-89.5° C.

Workup

  1. temperaturecooled in an ice bath
  2. additionAt the end of the addition
  3. customthe ice bath was removed
  4. stirringto stir at room temperature overnight (about 16 hours)
  5. additionThe product was poured onto 300 ml of ice
  6. extractionextracted with CHCl3 (300 ml)
  7. washwashed with water (500 ml portions), brine (500 ml)
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated
  10. customto give 39.9 g (96.4%) of crude material
  11. customTwo recrystallizations from isopropyl ether

Sources & evidence

ORD record
ord-60d521cdded749cf9f0e1a2577a2c3bb
Source dataset
uspto-grants-1985_07
Patent number
US04532333

Reaction notes

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