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

HRID 1373265Notes

Reaction equation

HRID 1373265 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-56886d37eb5b4e8791e7379ffde8a103
Source dataset
uspto-grants-2007_01
Patent number
US07160891B2

Reaction notes

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