Hydrochloric Acid → HCID 66936726, compound

HRID 1943648Notes

Reaction equation

HRID 1943648 reaction equation
[NH:1]1[CH2:6][CH2:5][O: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]=[C:19]([N+:23]([O-:25])=[O:24])[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:1]2[CH2:6][CH2:5][O:4][C:3]3[CH:7]=[N:8][CH:9]=[CH:10][C:2]2=3)=[O:16])[CH:18]=[C:19]([N+:23]([O-:25])=[O:24])[C:20]=1[O:21][CH3:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 219615362,3-Dihydro-1H-pyrido[3,4-b][1,4]oxazineHCID 86650557Benzoyl chloride, 3-chloro-4-methoxy-5-nitro-

Product 1

HCID 66936726HCID 66936726, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 10 ml flask, 2,3-dihydro-1H-pyrido[3,4-b][1,4]oxazine (57 mg, 0.42 mmol) and 3-chloro-4-methoxy-5-nitro-benzoyl chloride (117 mg, 0.47 mmol) were dissolved in dichloromethane. Triethylamine (0.29 ml, 2.1 mmol) was added thereto and then stirred at room temperature for 2 hours. After neutralizing with 1N hydrochloric acid solution, the reaction mixture was extracted with dichloromethane. The combined organic layer was dried over anhydrous sodium sulfate (Na2SO4) and filtered and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica with a solvent of ethyl acetate:n-hexane=1:2. The fractions containing the product were collected and evaporated to obtain yellow solid (118 mg, 81%).

Workup

  1. extractionthe reaction mixture was extracted with dichloromethane
  2. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate (Na2SO4)
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was purified by column chromatography on silica with a solvent of ethyl acetate
  6. additionThe fractions containing the product
  7. customwere collected
  8. customevaporated

Sources & evidence

ORD record
ord-a0be14f68bd6473189dc70f22f199d0d
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

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