HCID 21432747, compound → HCID 21432737, compound

HRID 2399109Notes

Reaction equation

HRID 2399109 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[NH:18][N:17]=[C:16]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:15]2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(OCC)(=O)C.[O-2].[O-2].[Mn+4]>[CH2:1]([O:8][C:9]([NH:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[N:18]=[N:17][C:16]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:15]2)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 21432747HCID 21432747, compound

Product 1

HCID 21432737HCID 21432737, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of ethyl 6-(benzyloxycarbonylamino)-1,4-dihydrocinnolin-3-yl carboxylate in ethyl acetate (obtained as described below) was heated to reflux temperature and manganese dioxide (20 g.) was added. The mixture was heated under reflux for 30 minutes, filtered, and the filtrate evaporated in vacuo to approximately 25 ml. Petroleum ether (b.p. 60°-80° C.; 75 ml.) was added and the mixture filtered to give, as solid residue, ethyl 6-(benzyloxycarbonylamino)cinnolin-3-yl carboxylate, m.p. 205° C.

Workup

  1. additionwas added
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 30 minutes
  4. filtrationfiltered
  5. customthe filtrate evaporated in vacuo to approximately 25 ml
  6. additionPetroleum ether (b.p. 60°-80° C.; 75 ml.) was added
  7. filtrationthe mixture filtered

Sources & evidence

ORD record
ord-260e817544fa4f06b07eab9cf8287dba
Source dataset
uspto-grants-1977_05
Patent number
US04027023

Reaction notes

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