Diethyl Ether → 2-Oxo-2,3-dihydro-1H-indole-5-carbonitrile

HRID 1387398Notes

Reaction equation

HRID 1387398 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=S)[CH:6]2C)#[N:2].[NH4+].[Cl-].C([O:18]CC)C>C1COCC1.[Zn]>[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:18])[CH2:6]2)#[N:2]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 194241955-Cyano-3-methylthiooxindole

Product 1

HCID 27733462-Oxo-2,3-dihydro-1H-indole-5-carbonitrile

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-cyano-3-methylthiooxindole (6.0 g, 29 mmol) in THF (100 mL) was stirred at room temperature and a saturated aqueous solution of NH4Cl (100 mL) added followed by activated zinc (25 g, 0.38 mol). The resulting mixture was stirred for 18 hours. The mixture was filtered through a pad of diatomaceous earth and the pad washed with THF (20 mL). The organic phase was separated, dried over anhydrous MgSO4 and the solvent evaporated to leave a tan solid. Trituration of this solid with diethyl ether gave 5-cyanooxindole a white solid, (4.1 g, 88%). 1H NMR (DMSO-d6) δ7.63 (d, 1H, J=8.4 Hz), 7.62 (s, 1H), 6.93 (d, 1H, J=8.4 Hz), 3.55 (s, 2H). MS (−ve ES) 157 (100), (M−H)

Workup

  1. filtrationThe mixture was filtered through a pad of diatomaceous earth
  2. washthe pad washed with THF (20 mL)
  3. customThe organic phase was separated
  4. dry with materialdried over anhydrous MgSO4
  5. customthe solvent evaporated
  6. customto leave a tan solid

Sources & evidence

ORD record
ord-71fabc0a7a8f4038ad584b163bf45bb3
Source dataset
uspto-grants-2001_07
Patent number
US06268391B1

Reaction notes

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