1-Methylindole → 5-Hydroxy-5-(1-methyl-3-indolyl)-2,4,6-(1H,3H,5H)pyrimidinetrione

HRID 66593

Reaction equation

HRID 66593 reaction equation
O.[NH:2]1[C:10](=[O:11])[C:8](=[O:9])[C:6](=[O:7])[NH:5][C:3]1=[O:4].[CH3:12][N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14]1>C(O)C>[OH:9][C:8]1([C:15]2[C:16]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:13]([CH3:12])[CH:14]=2)[C:6](=[O:7])[NH:5][C:3](=[O:4])[NH:2][C:10]1=[O:11]

Participants

4

Reactant 2

HCID 117811-MethylindoleHCID 167232,4,5,6(1H,3H)-Pyrimidinetetrone, monohydrate

Product 1

HCID 212712505-Hydroxy-5-(1-methyl-3-indolyl)-2,4,6-(1H,3H,5H)pyrimidinetrione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Alloxan hydrate (1.6 g., 0.01 mole) 1-methylindole (1.3 g., 0.01 mole) and ethanol (50 ml.) was combined and the mixture refluxed for 0.5 hour, then concentrated to half-volume, diluted with water and the resulting product recovered by filtration [2.7 g., Rf 0.5 (1:1 ethyl acetate:hexane/5% acetic acid)].

Workup

  1. temperaturethe mixture refluxed for 0.5 hour
  2. concentrationconcentrated to half-volume
  3. additiondiluted with water
  4. filtrationthe resulting product recovered by filtration [2.7 g., Rf 0.5 (1:1 ethyl acetate:hexane/5% acetic acid)]

Sources & evidence

ORD record
ord-b905210002c446778598a5214583d97f
Source dataset
uspto-grants-1982_08
Patent number
US04342771

Linked notes

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