HCID 15030135, compound → HCID 15030120, compound

HRID 1031266Notes

Reaction equation

HRID 1031266 reaction equation
[N:1]1([CH2:7][CH:8]2[N:13]3[C:14]([CH3:27])=[C:15](SC4C=CC=CC=4)[C:16]4[CH:17]=[CH:18][CH:19]=[C:11]([C:12]=43)[O:10][CH2:9]2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1>C(O)C.[Ni]>[N:1]1([CH2:7][CH:8]2[N:13]3[C:14]([CH3:27])=[CH:15][C:16]4[CH:17]=[CH:18][CH:19]=[C:11]([C:12]=43)[O:10][CH2:9]2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 15030135HCID 15030135, compound

Product 1

HCID 15030120HCID 15030120, compoundYield 61.6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a solution of 10.6 g (0.028 mole) of 3-(4-morpholinylmethyl)-5-methyl-6-phenylthio-2,3-dihydropyrrolo[1,2,3-de]-1,4-benzoxazine in 600 ml of ethanol was added seven teaspoons of Raney nickel. The mixture was heated under reflux for two hours and then filtered through filter aid. Evaporation of the filtrate to dryness and recrystallization of the residue from ethyl acetate afforded 4.7 g of 3-(4-morpholinylmethyl)-5-methyl-2,3-dihydropyrrolo[1,2,3-de]-1,4-benzoxazine, m.p. 178°-180° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for two hours
  3. filtrationfiltered
  4. filtrationthrough filter aid
  5. customEvaporation of the filtrate
  6. customto dryness and recrystallization of the residue from ethyl acetate

Sources & evidence

ORD record
ord-ad29d0944a484226831f4c9fc5e48b85
Source dataset
uspto-grants-1992_04
Patent number
US05109135

Reaction notes

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