4'-Methoxyacetophenone → HCID 15030131, compound

HRID 974137Notes

Reaction equation

HRID 974137 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.[CH3:19][C:20]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1)=[O:21].[CH:30](OC)=O.[H-].[Na+]>C(O)(=O)C.C(OCC)C.C(O)C.C(OCC)(=O)C>[N:1]1([CH2:7][CH:8]2[N:13]3[CH:30]=[C:19]([C:20](=[O:21])[C:22]4[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=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 4

HCID 74764'-MethoxyacetophenoneHCID 7865Methyl formateHCID 24758Sodium hydrideHCID 15169762HCID 15169762, compound

Product 1

HCID 15030131HCID 15030131, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-(4-morpholinylmethyl)-6-(4-methoxvbenzoyl)-2,3-dihydropyrrolo[1,2,3-de]-1,4-benzoxazine, m.p. 209°-214° C. (1.5 g from ethyl acetate) was prepared by reaction of 13 g (0.052 mole) of 3-(4-morpholinylmethyl)-4-amino-3,4-dihydro-2H-1,4-benzoxazine with 10.2 g (0.057 mole) 8-(4-methoxyphenyl)-8-ketopropionaldehyde in glacial acetic acid (the 8-ketopropionaldehyde being prepared by reaction of 4-methoxyacetophenone with methyl formate in diethyl ether in the presence of ethanol and sodium hydride).

Sources & evidence

ORD record
ord-3bea88a217d5427dad2026850adc900f
Source dataset
uspto-grants-1991_11
Patent number
US05066803

Reaction notes

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