Oxalyl chloride → 4,6-dimethoxy-2,3-dihydro-1H-indole-2,3-dione

HRID 641713Notes

Reaction equation

HRID 641713 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]([CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1)[NH2:7].[C:13](Cl)(=[O:17])[C:14](Cl)=[O:15]>CO>[CH3:12][O:11][C:9]1[CH:10]=[C:4]([O:3][CH3:2])[CH:5]=[C:6]2[C:8]=1[C:13](=[O:17])[C:14](=[O:15])[NH:7]2

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 218603Benzenamine, 3,5-dimethoxy-, hydrochloride (1:1)

Product 1

HCID 115575224,6-dimethoxy-2,3-dihydro-1H-indole-2,3-dione

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3,5-dimethoxyaniline hydrochloride (54.7 g), oxalyl chloride (54 ml) and methanol (500 ml) was stirred and heated to reflux for 1.5 hours. The mixture was cooled to ambient temperature. The precipitate was isolated, washed in turn with methanol and diethyl ether and dried under vacuum to give 4,6-dimethoxy-2,3-dioxoindoline (55 g); NMR Spectrum: (DMSOd6) 3.85 (s, 3H), 3.9 (s, 3H), 6.0 (s, 1H), 6.2 (s, 1H), 10.9 (s, 1H); Mass Spectrum: M+Na+ 230.

Workup

  1. temperatureheated
  2. temperatureto reflux for 1.5 hours
  3. customThe precipitate was isolated
  4. washwashed in turn with methanol and diethyl ether
  5. customdried under vacuum

Sources & evidence

ORD record
ord-ebaf7c995ae84510909314e46062a297
Source dataset
uspto-grants-2010_04
Patent number
US07696214B2

Reaction notes

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