Potassium Iodide → HCID 9861832, compound

HRID 1596534Notes

Reaction equation

HRID 1596534 reaction equation
[O:1]=[C:2]1[CH2:10][CH2:9][CH2:8][C:7]2[NH:6][C:5]([C:11]#[N:12])=[CH:4][C:3]1=2.[Cl:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][C:21]=1[Cl:22])[CH2:17]Cl.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCOCC>[Cl:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][C:21]=1[Cl:22])[CH2:17][N:6]1[C:7]2[CH2:8][CH2:9][CH2:10][C:2](=[O:1])[C:3]=2[CH:4]=[C:5]1[C:11]#[N:12]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 76093,4-Dichlorobenzyl chlorideHCID 11430Potassium CarbonateHCID 10261369HCID 10261369, compound

Product 1

HCID 9861832HCID 9861832, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

4-Oxo4,5,6,7-tetrahydroindol-2-carbonitrile (5.5 g) (Estep, K. G.; Synthetic Communications, 1995, 25, 507-514) in DMF (100 mL) was stirred with 3,4-dichlorobenzyl chloride (5.86 g), potassium iodide (cat.) and potassium carbonate (5.5 g) overnight until reaction was complete. The mixture was poured onto ice and partitioned between water and methylene chloride. The organic phase was washed with brine and dried (MgSO4), and the solvents removed in vacuo, to afford a pale yellow solid. Trituration with ether afforded the title compound as a white solid (8.71 g, 91%), NMR d(CDCl3) 2.20 (2H, dt), 2.50 (2H, t), 2.78 (2H, t), 5.20 (2H, s) 6.95 (1H, dd), 7.20 (2H, m), 7.45 (1H, d); M/z (+) 321 (MH+), 319.

Workup

  1. additionThe mixture was poured onto ice
  2. custompartitioned between water and methylene chloride
  3. washThe organic phase was washed with brine
  4. dry with materialdried (MgSO4)
  5. customthe solvents removed in vacuo
  6. customto afford a pale yellow solid

Sources & evidence

ORD record
ord-1d3d480d341844fcac43ce1f2a3b3438
Source dataset
uspto-grants-2001_09
Patent number
US06291507B1

Reaction notes

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