Ethanol → HCID 13885783, compound

HRID 580013Notes

Reaction equation

HRID 580013 reaction equation
Br[CH:2](Br)[C:3]1[NH:4][C:5]2[C:10]([CH:11]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:12]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:9]([O:24][CH:25]([CH3:27])[CH3:26])[N:8]=[CH:7][CH:6]=2.C([OH:31])C>O.[N+]([O-])([O-])=O.[Ag+]>[CH:2]([C:3]1[NH:4][C:5]2[C:10]([CH:11]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:12]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:9]([O:24][CH:25]([CH3:27])[CH3:26])[N:8]=[CH:7][CH:6]=2)=[O:31]

Participants

5

Reactant 2

HCID 702EthanolHCID 13885782HCID 13885782, compound

Product 1

HCID 13885783HCID 13885783, compound

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 962WaterSolvent

Procedure

A solution of 3.1 g (6.1 mMole) ethyl (±)-2-dibromomethyl-1,4-dihydro-5-isopropoxy-4-phenyl-1,6-naphthyridine-3-carboxylate (Example 4) in 70 ml ethanol is heated to 60° C. and, at this temperature, a solution of 2.1 g (12.4 mMole) silver nitrate in 5 ml water/3 ml ethanol is added dropwise thereto. The reaction mixture is heated under reflux for ten minutes, cooled and the precipitate filtered off, whereafter the filtrate is evaporated. After dilution with dichloromethane, it is washed with water and the organic phase is dried over anhydrous magnesium sulphate and subsequently evaporated in a vacuum. The residue is chromatographed on silica gel with toluene/ethyl acetate (9:1 v/v). The fraction with the Rf of 0.3 is isolated and recrystallized from n-hexane/cyclohexane. There is obtained ethyl (±)-2-formyl-1,4-dihydro-5-isopropoxy-4-phenyl-1,6-naphthyridine-3-carboxylate in the form of yellow crystals; mp 132°-135° C.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureunder reflux for ten minutes
  3. temperaturecooled
  4. filtrationthe precipitate filtered off, whereafter the filtrate
  5. customis evaporated
  6. washAfter dilution with dichloromethane, it is washed with water
  7. dry with materialthe organic phase is dried over anhydrous magnesium sulphate
  8. customsubsequently evaporated in a vacuum
  9. customThe residue is chromatographed on silica gel with toluene/ethyl acetate (9:1 v/v)
  10. customThe fraction with the Rf of 0.3 is isolated
  11. customrecrystallized from n-hexane/cyclohexane

Sources & evidence

ORD record
ord-78be3f54a185420bab8215f38e2e35d1
Source dataset
uspto-grants-1988_06
Patent number
US04751228

Reaction notes

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