Sodium Carbonate → HCID 15030130, compound

HRID 1031270Notes

Reaction equation

HRID 1031270 reaction equation
[N:1]1([CH2:7][CH:8]2[N:13](N)[C:12]3[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=3[O:10][CH2:9]2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Na].[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([C:28](=[O:34])[CH2:29][C:30](=O)[CH2:31][CH3:32])=[CH:24][CH:23]=1.C(=O)([O-])[O-].[Na+].[Na+].C(=O)(O)[O-].[Na+]>C(O)(=O)C.C(OCC)(=O)C.O>[N:1]1([CH2:7][CH:8]2[N:13]3[C:30]([CH2:31][CH3:32])=[C:29]([C:28](=[O:34])[C:25]4[CH:26]=[CH:27][C:22]([O:21][CH3:20])=[CH:23][CH:24]=4)[C:15]4[CH:16]=[CH:17][CH:18]=[C:11]([C:12]=43)[O:10][CH2:9]2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

9

Reactant 5

HCID 10340Sodium CarbonateHCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 15169762HCID 15169762, compoundHCID 15169783HCID 15169783, compound

Product 1

HCID 15030130HCID 15030130, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 22.2 g (0.089 mole) of 3-(4-morpholinylmethyl)-4-amino-3,4-dihydro-2H-1,4-benzoxazine and 18.3 g (0.08 mole) of the sodium salt of 5-(4-methoxyphenyl)-3,5-pentanedione in 250 ml of glacial acetic acid was heated under reflux for four hours, then cooled and poured into 1500 ml of water and 600 ml of ethyl acetate. The mixture was neutralized by the addition of solid sodium carbonate and solid sodium bicarbonate with stirring, the organic layer was separated from the aqueous layer and dried over magnesium sulfate, filtered and taken to dryness. The crude product was purified by chromatography on silica gel, eluting with 4:1 hexane/ethyl acetate, the first 700 ml of eluate being discarded, and the next 800 ml, containing the product, being retained. Evaporation of the latter to dryness and recrystallization of the residue from ethyl acetate afforded 3.9 g of 3-(4-morpholinylmethyl)-5-ethyl-6-(4-methoxybenzoyl)-2,3-dihydropyrrolo[1,2,3-de]-1,4-benzoxazine, m.p. 185.5°- 187.0° C.

Workup

  1. temperatureunder reflux for four hours
  2. temperaturecooled
  3. customthe organic layer was separated from the aqueous layer
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customThe crude product was purified by chromatography on silica gel
  7. washeluting with 4:1 hexane/ethyl acetate
  8. additionthe next 800 ml, containing the product
  9. customEvaporation of the
  10. customlatter to dryness and recrystallization of the residue from ethyl acetate

Sources & evidence

ORD record
ord-27e497427afa4f90838ff76079470ff5
Source dataset
uspto-grants-1992_04
Patent number
US05109135

Reaction notes

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