Water → HCID 17963940, compound

HRID 1375030Notes

Reaction equation

HRID 1375030 reaction equation
[O:1]1[CH2:6][CH2:5][NH:4][C:3]2[N:7]=[CH:8][CH:9]=[CH:10][C:2]1=2.[H-].[Na+].Cl[CH2:14][CH:15]1[O:19][CH2:18][CH2:17][O:16]1.O>CN(C)C=O.C(OCC)(=O)C>[O:16]1[CH2:17][CH2:18][O:19][CH:15]1[CH2:14][N:4]1[CH2:5][CH2:6][O:1][C:2]2[CH:10]=[CH:9][CH:8]=[N:7][C:3]1=2

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 757272-(Chloromethyl)-1,3-dioxolaneHCID 131965383,4-Dihydro-2H-pyrido(3,2-b)(1,4)oxazine

Product 1

HCID 17963940HCID 17963940, compoundYield 42.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3,4-dihydro-2H-pyrido[3,2-b]-1,4-oxazine (0.4 g) in N,N-dimethylformamide (5 ml) was added sodium hydride (60% oil suspension; 0.24 g) in portions. After a few minutes, a solution of 2-chloromethyl-1,3-dioxolane (0.43 g) in N,N-dimethylformamide (2 ml) was added dropwise to the mixture. After stirring for 2 hours, the mixture was poured into a mixed solvent of water and ethyl acetate. The organic layer was separated, washed with water twice, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixed solvent of ethyl acetate and hexane (1:1) as an eluent to give 3,4-dihydro-4-[(1,3-dioxolan-2-yl)methyl]-2H-pyrido[3,2-b]-1,4-oxazine (0.28 g) as an oil.

Workup

  1. waitAfter a few minutes
  2. customThe organic layer was separated
  3. washwashed with water twice
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel using a mixed solvent of ethyl acetate and hexane (1:1) as an eluent

Sources & evidence

ORD record
ord-36b9c7b9d91f4203a3065d62132580c1
Source dataset
uspto-grants-2007_01
Patent number
US07166598B2

Reaction notes

Loading…