HCID 21432700, compound → HCID 21432735, compound

HRID 2399112Notes

Reaction equation

HRID 2399112 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[NH:15][N:14]=[C:13]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:12]2>C(OCC)(=O)C.[O-2].[O-2].[Mn+4]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[N:14][C:13]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:12]2

Participants

4

Reactant 1

HCID 21432700HCID 21432700, compound

Product 1

HCID 21432735HCID 21432735, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of ethyl 6-(methoxyphenyl)-1,4-dihydrocinnolin-3-yl carboxylate in ethyl acetate (obtained as described below) was heated to boiling point and manganese dioxide (15 g.) was added. The mixture was heated under reflux for 30 minutes and then filtered. The filtrate was evaporated to approx. 1 ml. in vacuo and the residue was applied to a silica column (30 g. Kieselgel 60). The column was eluted with a 50% v/v mixture of ethyl acetate and petroleum ether (b.p. 60°-80° C.). The appropriate fractions were combined and evaporated in vacuo, and the crystalline residue was recrystallised from aqueous ethanol to give ethyl 6-(methoxyphenyl)cinnolin-3-yl carboxylate m.p. 143°-145° C. (believed to be a mixture of isomers varying in the position of the methoxy radical on the phenyl substituent).

Workup

  1. additionwas added
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 30 minutes
  4. filtrationfiltered
  5. customThe filtrate was evaporated to approx. 1 ml
  6. washThe column was eluted with a 50% v/v mixture of ethyl acetate and petroleum ether (b.p. 60°-80° C.)
  7. customevaporated in vacuo
  8. customthe crystalline residue was recrystallised from aqueous ethanol

Sources & evidence

ORD record
ord-f8763090888f4a769bb96dfe353a3ae0
Source dataset
uspto-grants-1977_05
Patent number
US04027023

Reaction notes

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