4'-Methoxyacetophenone → HCID 15030131, compound

HRID 1031273Notes

Reaction equation

HRID 1031273 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][O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27](=[O:31])[CH2:28][CH:29]=O)=[CH:23][CH:22]=1.O=CCC=O.CC(C1C=CC(OC)=CC=1)=O.C(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:29]=[C:28]([C:27](=[O:31])[C:24]4[CH:25]=[CH:26][C:21]([O:20][CH3:19])=[CH:22][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

11

Reactant 6

HCID 74764'-MethoxyacetophenoneHCID 7865Methyl formateHCID 10964MalonaldehydeHCID 24758Sodium hydrideHCID 12650746HCID 12650746, compoundHCID 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-methoxybenzoyl)-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) β-(4-methoxyphenyl)-β-ketopropionaldehyde in glacial acetic acid (the β-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-5383579ef8b8418e8466c41007214b78
Source dataset
uspto-grants-1992_04
Patent number
US05109135

Reaction notes

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