Potassium Iodide → HCID 22310865, compound

HRID 413787Notes

Reaction equation

HRID 413787 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[C:7]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[NH:8]2)([O-:3])=[O:2].[Cl:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][C:26]=1[Cl:27])[CH2:22]Cl.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C=O)C>[Cl:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][C:26]=1[Cl:27])[CH2:22][N:8]1[C:9]2[C:5](=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=[CH:11][CH:10]=2)[CH:6]=[C:7]1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 76093,4-Dichlorobenzyl chlorideHCID 11430Potassium CarbonateHCID 283173Ethyl 4-nitro-1H-indole-2-carboxylate

Product 1

HCID 22310865HCID 22310865, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 4-nitroindole-2-carboxylate (26 g) [prepared according to S. M. Parmerter el. al. J. Amer. Chem. Soc., 1958, 80, 4621], 3,4-dichlorobenzyl chloride (16 ml), potassium carbonate (17 g) and potassium iodide (2 g) in DMF (250 ml) were stirred at 60° C. for 2 hours. The reaction was concentrated in vacuo and the residue partitioned between water and dichloromethane. Iso-hexane was added to the combined organic extracts resulting in crystallisation of the product as yellow needles (39 g. 89%) NMR d (CD3SOCD3) 1.30 (t, 3H), 4.32 (q, 2H), 5.93 (s, 2H), 6.88 (dd, 1H), 7.18 (d, 1H), 7.52 (d, 1H), 7.56 (dd, 1H), 7.78 (s, 1H), 8.17 (m, 2H); M/z (+) 395 (MH+), 393.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customthe residue partitioned between water and dichloromethane
  3. additionIso-hexane was added to the combined organic extracts

Sources & evidence

ORD record
ord-3e2332d3269e4e67b7449a81af05eb17
Source dataset
uspto-grants-2003_05
Patent number
US06569888B1

Reaction notes

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