Hydrochloric Acid → HCID 66936726, compound

HRID 1943680Notes

Reaction equation

HRID 1943680 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 83.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 10 ml flask, 2,3-dihydro-1H-pyrido[3,4-b][1,4]oxazine (96.2 mg, 0.706 mmol) and 3-chloro-4-methoxy-5-nitro-benzoyl chloride (194 mg, 0.777 mmol) were dissolved in dichloromethane (3 ml). Triethylamine (0.15 ml, 1.059 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 yellow solid (206 mg, 83.4%).

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-b89c8aa80e4c451b8392cbd36fbcbd83
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

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