3,4-Dichlorobenzyl chloride → HCID 22310865, compound

HRID 1072564Notes

Reaction equation

HRID 1072564 reaction equation
[OH-].[Na+].[N+:3]([C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[C:9]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[NH:10]2)([O-:5])=[O:4].[Cl:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][C:28]=1[Cl:29])[CH2:24]Cl>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[Cl:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][C:28]=1[Cl:29])[CH2:24][N:10]1[C:11]2[C:7](=[C:6]([N+:3]([O-:5])=[O:4])[CH:14]=[CH:13][CH:12]=2)[CH:8]=[C:9]1[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

6

Reactant 3

HCID 76093,4-Dichlorobenzyl chlorideHCID 14798Sodium HydroxideHCID 283173Ethyl 4-nitro-1H-indole-2-carboxylate

Product 1

HCID 22310865HCID 22310865, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

Sodium hydroxide (3M, 20 ml) was added to a vigorously stirred solution of ethyl 4-nitroindole-2-carboxylate (4 g), 3,4-dichlorobenzyl chloride (4.73 ml) and tetra-n-butylammonium hydrogensulphate (0.2 g) in dichloromethane (60 ml). The reaction was stirred for 48 hours then partitioned between 2M HCl and dichloromethane. Combined organic extracts were dried (MgSO4) and concentrated in vacuo and the residue purified by column chromatography using iso-hexane: 20% ethyl acetate as eluent to give the product as a yellow crystalline solid (5.26 g, 78%); NMR δ (CD3SOCD3) 1.3 (t, 3H), 4.3 (q, 2H), 5.95 (s, 2H), 6.9 (m, 1H), 7.6 (m, 4H), 8.2 (t, 2H); M/z (+) 393.3 (M+).

Workup

  1. customthen partitioned between 2M HCl and dichloromethane
  2. dry with materialCombined organic extracts were dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-6443e55503fd46ceb9f384eb88118515
Source dataset
uspto-grants-2005_06
Patent number
US06911465B1

Reaction notes

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