o-Chloranil → HCID 58624130, compound

HRID 1354592Notes

Reaction equation

HRID 1354592 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([C@H:12]([OH:15])[CH2:13][Cl:14])=[CH:8][C:9]=2[Cl:11])[CH2:4][CH2:3]1.C1(Cl)C(Cl)=C(Cl)C(=O)C(=O)C=1Cl>COC(C)(C)C>[Cl:14][CH2:13][C@H:12]([C:7]1[CH:6]=[C:5]2[C:10](=[C:9]([Cl:11])[CH:8]=1)[N:2]([CH3:1])[CH:3]=[CH:4]2)[OH:15]

Participants

4

Reactant 2

HCID 73252o-ChloranilHCID 23541644HCID 23541644, compound

Product 1

HCID 58624130HCID 58624130, compound

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

A solution (S)-N-Methyl-5-(2-chloro-1-hydroxylethyl)-7-chloro-indoline (0.10 mmol) in 100 mL of t-butyl methyl ether is treated with o-chloroanil (0.10 mmol) at ambient temperature. The solution is concentrated and the residue chromatographed over silica gel (1:1 hexane/ethyl acetate) to provide the corresponding indole.

Workup

  1. concentrationThe solution is concentrated
  2. customthe residue chromatographed over silica gel (1:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-6b9a448ead6341558ba8813f4a1837b1
Source dataset
uspto-grants-2007_05
Patent number
US07223757B2

Reaction notes

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