p-Anisoyl chloride → HCID 15030121, compound

HRID 1031268Notes

Reaction equation

HRID 1031268 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][O:6][C:7]1[CH:15]=[CH:14][C:10]([C:11](Cl)=[O:12])=[CH:9][CH:8]=1.[N:16]1([CH2:22][CH:23]2[N:28]3[C:29]([CH3:35])=[CH:30][C:31]4[CH:32]=[CH:33][CH:34]=[C:26]([C:27]=43)[O:25][CH2:24]2)[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1>C(Cl)Cl>[N:16]1([CH2:22][CH:23]2[N:28]3[C:29]([CH3:35])=[C:30]([C:11](=[O:12])[C:10]4[CH:14]=[CH:15][C:7]([O:6][CH3:5])=[CH:8][CH:9]=4)[C:31]4[CH:32]=[CH:33][CH:34]=[C:26]([C:27]=43)[O:25][CH2:24]2)[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 7477p-Anisoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 15030120HCID 15030120, compound

Product 1

HCID 15030121HCID 15030121, compoundYield 47.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 7.5 g (0.056 mole) of aluminum chloride in 100 ml of methylene dichloride (MDC) was added, rapidly with stirring, a solution of 6.2 ml (0.038 mole) of 4-methoxybenzoyl chloride. When addition was complete the mixture was stirred for one hour at room temperature and the resulting solution then added dropwise over a ten minute period with stirring to a solution of 8.5 g (0.031 mole) of 3-(4-morpholinylmethyl)-5-methyl-2,3-dihydropyrrolo-[1,2,3-de]-1,4-benzoxazine in 100 ml of MDC. The resulting mixture was then heated under reflux for thirty minutes, cooled and poured into 300 ml of ice water with stirring. The organic solvent was removed in vacuo, and the residual aqueous medium was diluted with ethyl acetate and neutralized by the addition of saturated aqueous sodium bicarbonate. The organic layer was separated, dried over magnesium sulfate, filtered through silica, taken to dryness in vacuo and chromatographed on silica gel, eluting with 1:1 hexane:ethyl acetate. There was thus obtained about 7 g of crude product which was recrystallized from ethyl acetate/hexane to give 6.0 g of 3-(4-morpholinylmethyl)-5-methyl-6-(4-methoxybenzoyl)-2,3-dihydropyrrolo[1,2,3-de]-1,4-benzoxazine, m.p. 182°-189° C.

Workup

  1. additionwas added
  2. additionWhen addition
  3. stirringwas stirred for one hour at room temperature
  4. additionthe resulting solution then added dropwise over a ten minute period
  5. temperatureThe resulting mixture was then heated
  6. temperatureunder reflux for thirty minutes
  7. temperaturecooled
  8. stirringwith stirring
  9. customThe organic solvent was removed in vacuo
  10. additionthe residual aqueous medium was diluted with ethyl acetate
  11. additionneutralized by the addition of saturated aqueous sodium bicarbonate
  12. customThe organic layer was separated
  13. dry with materialdried over magnesium sulfate
  14. filtrationfiltered through silica
  15. customchromatographed on silica gel
  16. washeluting with 1:1 hexane
  17. customwas recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-8997a0d9c24647c1b33dd7f22605f379
Source dataset
uspto-grants-1992_04
Patent number
US05109135

Reaction notes

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