Ammonia → HCID 20028484, compound

HRID 1722248Notes

Reaction equation

HRID 1722248 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]([CH3:15])[CH:8]=[C:7]([C:16](OCC)=[O:17])[C:6]2=[O:21].[NH3:22]>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]([CH3:15])[CH:8]=[C:7]([C:16]([NH2:22])=[O:17])[C:6]2=[O:21]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 15675311HCID 15675311, compound

Product 1

HCID 20028484HCID 20028484, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 6,7-dimethoxy-1-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate (4.0 g) and ethanol saturated with ammonia (200 ml) was heated at 100° in a stainless steel pressure vessel for 20 hours, then cooled to ambient temperature. The mixture was evaporated and the residue purified by high pressure liquid chromatography on silica using dichloromethane IMS 96.5:3.5 as the eluent. The resulting product was recrystallised from IMS to give the novel compound 6,7-dimethoxy-1-methyl-4-oxo-1,4-dihydroquinoline-3-carboxamide, m.p. 323°-325° (dec).

Workup

  1. temperaturewas heated at 100° in a stainless steel pressure vessel for 20 hours
  2. customThe mixture was evaporated
  3. customthe residue purified by high pressure liquid chromatography on silica
  4. customThe resulting product was recrystallised from IMS

Sources & evidence

ORD record
ord-c107e4b8c19747af9a257d135e858cbc
Source dataset
uspto-grants-1989_08
Patent number
US04855291

Reaction notes

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