Acetone → HCID 19735125, compound

HRID 326593Notes

Reaction equation

HRID 326593 reaction equation
[NH3:1].[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([C:10]1[C:19]([OH:20])=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1)=O.[Cl-].[NH4+].S([O-])([O-])(=O)=O.[Ca+2].[CH3:29][C:30]([CH3:32])=O>>[CH3:29][C:30]1([CH3:32])[N:1]=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][N:2]=2)[C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][C:19]=2[O:20]1)[CH:16]=[CH:15][CH:14]=[CH:13]3

Participants

6

Reactant 5

HCID 180AcetoneHCID 222AmmoniaHCID 24497Calcium SulfateHCID 25517Ammonium ChlorideHCID 54049854HCID 54049854, compound

Product 1

HCID 19735125HCID 19735125, compound

Conditions

Temperature
85 °C

Procedure

To acetone (3 ml) saturated with ammonia were added 3-hydroxy-2-naphthyl 2-pyridyl ketone (30 mg, mp.104°-109° C.), ammonium chloride (6 mg) and anhydrous calcium sulfate (30 mg) at room temperature. The mixture was stirred for 4 hours at 85° C. in a sealed tube. The insoluble substance in the reaction mixture was filtered off. Aqueous saturated ammonium chloride solution was added to the filtrate and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off. The residue was purified by column chromatography on silica gel and eluted with ethyl acetate/hexane to obtain 2,2-dimethyl-4-(2-pyridyl)-2H-naphtho[2,3-e][1,3]oxazine (18 mg) (Compound 82).

Workup

  1. filtrationThe insoluble substance in the reaction mixture was filtered off
  2. additionAqueous saturated ammonium chloride solution was added to the filtrate
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off
  7. customThe residue was purified by column chromatography on silica gel
  8. washeluted with ethyl acetate/hexane

Sources & evidence

ORD record
ord-bf8d74c8fb1d4ae9b65de36818ee8d5b
Source dataset
uspto-grants-1993_12
Patent number
US05270308

Reaction notes

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