Sodium Hydroxide → HCID 22310859, compound

HRID 413788Notes

Reaction equation

HRID 413788 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[Cl:26])[CH2:5][N:6]1[C:14]2[C:9](=[C:10]([N+:15]([O-])=O)[CH:11]=[CH:12][CH:13]=2)[CH:8]=[C:7]1[C:18]([O:20][CH2:21][CH3:22])=[O:19].[OH-].[Na+]>O1CCCC1.[Cl-].[Cl-].[Cl-].[Ti+3]>[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[Cl:26])[CH2:5][N:6]1[C:14]2[C:9](=[C:10]([NH2:15])[CH:11]=[CH:12][CH:13]=2)[CH:8]=[C:7]1[C:18]([O:20][CH2:21][CH3:22])=[O:19]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22310865HCID 22310865, compound

Product 1

HCID 22310859HCID 22310859, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 10313229titanium(III) trichlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl N-(3,4-dichlorobenzyl)-4-nitroindole-2-carboxylate (2.41 g) in tetrahydrofuran (100 ml) was stirred in the presence of titanium trichloride (15% aqueous solution, 50 ml) at room temperature overnight. The reaction was treated with 40% sodium hydroxide solution and extracted with 5% methanol in dichloromethane. Combined organic extracts were dried (MgSO4) and concentrated in vacuo to give the product as a brown solid (1.98 g, 89%); NMR d (CD3SOCD3) 1.3 (t, 3H), 4.2 (q, 2H), 5.7 (s, 4H), 6.2 (d, 1H), 6.6 (d, 1H), 7.0 (m, 1H), 7.25 (m, 1H), 7.5 (d, 1H), 7.6 (m, 1H): M/z (+) 363.3 (MH+).

Workup

  1. extractionextracted with 5% methanol in dichloromethane
  2. dry with materialCombined organic extracts were dried (MgSO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f6e59798b0004b78a465102e176cc635
Source dataset
uspto-grants-2003_05
Patent number
US06569888B1

Reaction notes

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