Hydrochloric Acid → HCID 66936690, compound

HRID 1943676Notes

Reaction equation

HRID 1943676 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]=[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: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]=[CH:19][C:20]=1[O:21][CH3:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 47692993-Chloro-4-methoxybenzoyl chlorideHCID 219615362,3-Dihydro-1H-pyrido[3,4-b][1,4]oxazine

Product 1

HCID 66936690HCID 66936690, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 10 ml flask, 2,3-dihydro-1H-pyrido[3,4-b][1,4]oxazine (60 mg, 0.441 mmol) and 3-chloro-4-methoxy-benzoyl chloride (108 mg, 0.529 mmol) were dissolved in dichloromethane (3 ml). Triethylamine (0.12 ml, 0.881 mmol) was added thereto and then stirred at room temperature for 2 hours. After neutralizing with 1N hydrochloric acid solution, the mixture was extracted with dichloromethane, and the combined organic layer was dried over anhydrous sodium sulfate (Na2SO4), filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica eluting with a solvent of ethyl acetate:n-hexane=1:1. The fractions containing the product were collected and evaporated to obtain white solid (134 mg, 99.8%).

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. dry with materialthe combined organic layer was dried over anhydrous sodium sulfate (Na2SO4)
  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-21df6349b9dd40eea122ffbc28de0df0
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

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