HCID 15030135, compound → HCID 15030120, compound

HRID 2165459Notes

Reaction equation

HRID 2165459 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-ef5c33b50ead4143967da18df8213461
Source dataset
uspto-grants-1990_07
Patent number
US04939138

Reaction notes

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