Potassium Carbonate → HCID 178519726, compound

HRID 1943674Notes

Reaction equation

HRID 1943674 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.S(Cl)(Cl)=O.[O:15]1[CH2:20][CH2:19][NH:18][C:17]2[CH:21]=[N:22][CH:23]=[CH:24][C:16]1=2.C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])O.[Na+]>CN(C)C(=O)C.C(OCC)(=O)C>[O:15]1[CH2:20][CH2:19][N:18]([C:6]([C:5]2[CH:4]=[N:3][C:2]([OH:1])=[CH:10][CH:9]=2)=[O:8])[C:17]2[CH:21]=[N:22][CH:23]=[CH:24][C:16]1=2

Participants

8

Reactant 5

HCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 218859502H,3H,4H-pyrido[4,3-b][1,4]oxazineHCID 178418479HCID 178418479, compound

Product 1

HCID 178519726HCID 178519726, compoundYield 45.8%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

In a 25 ml flask, 6-hydroxy-nicotinic acid (102 mg, 0.73 mmol) was dissolved in N,N-dimethyl acetamide (2.7 ml) and then cooled to −15□. Thionyl chloride (0.06 ml) was added thereto and the temperature was slowly raised up to −5□ and then stirred at −5□ for 30 minutes. The mixture was cooled again to −15□ and then 3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazine (100 mg, 0.73 mmol) and potassium carbonate (127 mg, 0.82 mmol) were added thereto and stirred for 10 minutes. The temperature was raised up to room temperature and then stirred for 14 hours. Ethyl acetate was added to the reaction mixture, and the mixture was neutralized with saturated solution of sodium hydrogen carbonate and evaporated under reduced pressure. The residue was purified by column chromatography on amine silica eluting with a solvent of dichloromethane:methanol=50:1. The fractions containing the product were collected and evaporated to obtain the target compound 32 as white solid (86 mg, 45%).

Workup

  1. temperaturecooled to −15□
  2. temperaturethe temperature was slowly raised up to −5□ and
  3. additionwere added
  4. stirringstirred for 10 minutes
  5. stirringstirred for 14 hours
  6. customevaporated under reduced pressure
  7. customThe residue was purified by column chromatography on amine silica eluting with a solvent of dichloromethane
  8. additionThe fractions containing the product
  9. customwere collected
  10. customevaporated

Sources & evidence

ORD record
ord-ae3fa98dc0d74def95f8876ba5fa916e
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

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