Ammonia → 2-Methoxy-7,8-dihydro-1,6-naphthyridin-5(6H)-one

HRID 533140Notes

Reaction equation

HRID 533140 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[N:6][C:5]=1[CH:12]=[CH2:13].[NH3:15]>CO>[CH3:11][O:10][C:7]1[CH:8]=[CH:9][C:4]2[C:3](=[O:2])[NH:15][CH2:13][CH2:12][C:5]=2[N:6]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 68008857HCID 68008857, compound

Product 1

HCID 680081312-Methoxy-7,8-dihydro-1,6-naphthyridin-5(6H)-oneYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 6-methoxy-2-vinyl-nicotinic acid methyl ester (130 g, 674 mmol) in 7M solution of NH3 in MeOH (500 mL) was added to a sealed vessel. The mixture was stirred at 100° C. for 24 h. The solvent was evaporated in vacuo. The crude product was diluted with MeOH and the mixture was stirred at rt. The solid was filtered and dried in vacuo to yield 2-methoxy-7,8-dihydro-1,6-naphthyridin-5(6H)-one (75 g, 63%) as a solid.

Workup

  1. additionwas added to a sealed vessel
  2. customThe solvent was evaporated in vacuo
  3. additionThe crude product was diluted with MeOH
  4. stirringthe mixture was stirred at rt
  5. filtrationThe solid was filtered
  6. customdried in vacuo

Sources & evidence

ORD record
ord-a87d521c609c4bfcb995e33be38945b5
Source dataset
uspto-grants-2014_10
Patent number
US08853237B2

Reaction notes

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