3-Ethoxy-2-methyl-6-(2,2-diethoxycarbonylethenyl)aminopyridine → Ethyl 6-ethoxy-4-hydroxy-7-methyl-1,8-naphthyridine-3-carboxylate

HRID 847771Notes

Reaction equation

HRID 847771 reaction equation
[CH2:1]([O:3][C:4]1[C:5]([CH3:23])=[N:6][C:7]([NH:10][CH:11]=[C:12]([C:18]([O:20]CC)=O)[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:8][CH:9]=1)[CH3:2]>C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>[CH2:1]([O:3][C:4]1[CH:9]=[C:8]2[C:7](=[N:6][C:5]=1[CH3:23])[N:10]=[CH:11][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:18]2[OH:20])[CH3:2]

Participants

3

Reactant 1

HCID 128750183-Ethoxy-2-methyl-6-(2,2-diethoxycarbonylethenyl)aminopyridine

Product 1

HCID 178469690Ethyl 6-ethoxy-4-hydroxy-7-methyl-1,8-naphthyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)Solvent

Procedure

16.1 g of the Compound VI obtained as above was added to 160 ml of boiling Dowtherm (produced by Dow Chemical Co.) and refluxed for 1 hour. After cooling, the precipitated crystals were collected by filtration to obtain 11.8 g of crude crystals which were then recrystallized from dimethylformamide to yield ethyl 6-ethoxy-4-hydroxy-7-methyl-1,8-naphthyridine-3-carboxylate (Compound VII where R2 =R3 =C2H5), m.p. 279°-282° C. (with decomposition).

Workup

  1. temperaturerefluxed for 1 hour
  2. temperatureAfter cooling
  3. filtrationthe precipitated crystals were collected by filtration
  4. customto obtain 11.8 g of crude crystals which
  5. customwere then recrystallized from dimethylformamide

Sources & evidence

ORD record
ord-06ed29e55c7f4346a522b66aacd0fc10
Source dataset
uspto-grants-1981_10
Patent number
US04293695

Reaction notes

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