Potassium Hydroxide → 4-hydroxy-1-(3-nitrophenyl)-1,8-naphthyridin-2(1H)-one

HRID 1822191Notes

Reaction equation

HRID 1822191 reaction equation
C(OC([C:6]1[C:7](=[O:26])[N:8]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=2)[C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][CH:12]=[CH:11][N:10]=2)=O)C.[OH-].[K+]>>[OH:16][C:15]1[C:14]2[C:9](=[N:10][CH:11]=[CH:12][CH:13]=2)[N:8]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=2)[C:7](=[O:26])[CH:6]=1

Participants

3

Reactant 2

HCID 14797Potassium HydroxideHCID 546762103-ethoxycarbonyl-4-hydroxy-1-(3-nitrophenyl)-1,8-naphthyridin-2(1H)-one

Product 1

HCID 546762034-hydroxy-1-(3-nitrophenyl)-1,8-naphthyridin-2(1H)-oneYield 100.2%

Procedure

To 3-ethoxycarbonyl-4-hydroxy-1-(3-nitrophenyl)-1,8-naphthyridin-2 (1H)-one (4.42 g, 12.4 mmol) was added an aqueous solution (18 ml) of potassium hydroxide (2.44 g, 43.4 mmol), and the mixture was heated under reflux overnight, treated with activated carbon (150 mg), refluxed for 10 minutes, and filtered off. The resultant solution was acidified to pH1 with hydrochloric acid, filtered off to give precipitates which were washed with water and dried to afford 4-hydroxy-1-(3-nitrophenyl)-1,8-naphthyridin-2 (1H)-one (3.52 g, quantitative) as crystals.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight
  3. additiontreated with activated carbon (150 mg)
  4. temperaturerefluxed for 10 minutes
  5. filtrationfiltered off
  6. filtrationfiltered off
  7. customto give
  8. customprecipitates which
  9. washwere washed with water
  10. customdried

Sources & evidence

ORD record
ord-9e2f4be82f7c4f0e95c77f226ea94f30
Source dataset
uspto-grants-2009_10
Patent number
US07608716B2

Reaction notes

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