Hydrochloric Acid → (3-Chloro-4-methoxy-phenyl)-(2,3-dihydro-pyrido[4,3-b][1,4]oxazin-4-yl)-methanone

HRID 1943643Notes

Reaction equation

HRID 1943643 reaction equation
[O:1]1[CH2:6][CH2:5][NH:4][C:3]2[CH:7]=[N:8][CH:9]=[CH:10][C:2]1=2.[Cl:11][C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[C:15](Cl)=[O:16].C(N(CC)CC)C.Cl>ClCCl>[Cl:11][C:12]1[CH:13]=[C:14]([C:15]([N:4]2[CH2:5][CH2:6][O:1][C:2]3[CH:10]=[CH:9][N:8]=[CH:7][C:3]2=3)=[O:16])[CH:18]=[CH:19][C:20]=1[O:21][CH3:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 47692993-Chloro-4-methoxybenzoyl chlorideHCID 218859502H,3H,4H-pyrido[4,3-b][1,4]oxazine

Product 1

HCID 66936357(3-Chloro-4-methoxy-phenyl)-(2,3-dihydro-pyrido[4,3-b][1,4]oxazin-4-yl)-methanoneYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 10 ml flask, 3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazine (150 mg, 1.102 mmol) and 3-chloro-4-methoxy-benzoyl chloride (249 mg, 1.212 mmol) were dissolved in dichloromethane. Triethylamine (0.77 ml, 5.510 mmol) was added thereto and then stirred at room temperature for 2 hours. The reaction mixture was neutralized with 1N hydrochloric acid solution and extracted with dichloromethane. And 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 ethyl acetate. The fractions containing the product were collected and evaporated to obtain ivory-colored solid (238 mg, 71%).

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialAnd the 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 ethyl acetate
  6. additionThe fractions containing the product
  7. customwere collected
  8. customevaporated

Sources & evidence

ORD record
ord-5693712d310044fd928c1c3c8a931925
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

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