Water → 2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-7-carbonitrile

HRID 1943695Notes

Reaction equation

HRID 1943695 reaction equation
Br[C:2]1[CH:11]=[N:10][C:5]2[O:6][CH2:7][CH2:8][NH:9][C:4]=2[CH:3]=1.O.[CH3:13][N:14]1CCCC1=O>>[NH:9]1[CH2:8][CH2:7][O:6][C:5]2[N:10]=[CH:11][C:2]([C:13]#[N:14])=[CH:3][C:4]1=2

Participants

4

Reactant 3

HCID 962WaterHCID 13387N-methyl-2-pyrrolidoneHCID 667890617-bromo-1H,2H,3H-pyrido[2,3-b][1,4]oxazine

Product 1

HCID 669365332,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-7-carbonitrile

Procedure

In a 5 ml flask, 7-bromo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine (24 mg, 0.111 mmol) was dissolved in N-methylpyrrolidone (NMP) (20.3 ml), and cuprous cyanide (CuCN) (16 mg, 0.178 mmol) was added thereto and then stirred in microwave at 180□ for 10 minutes using microwave (100 W) apparatus. The reaction mixture was cooled to room temperature and water (10 ml) was added thereto, and extracted with ethyl acetate (10 ml*2). The combined organic layer was dried over anhydrous magnesium sulfate (MgSO4), filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica eluting with a solvent of dichloromethane:methanol=20:1. The fractions containing the product were collected and evaporated to obtain pale-yellow solid (17 mg, quantitative yield).

Workup

  1. extractionextracted with ethyl acetate (10 ml*2)
  2. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate (MgSO4)
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica eluting with a solvent of dichloromethane
  6. additionThe fractions containing the product
  7. customwere collected
  8. customevaporated

Sources & evidence

ORD record
ord-f103f1e3fe1d4454906e7b55d9eeed9e
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

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