3,4-Dihydro-2H-1,4-benzoxazine → 4-(3,4-Dihydro-2H-1,4-benzoxazin-4-yl)-1-(3,4-dimethoxybenzoyl)-2-methyl-1,2,3,4-tetrahydroquinoline

HRID 585361Notes

Reaction equation

HRID 585361 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[C:6]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C@H:11](O)[CH2:10][C@@H:9]1[CH3:19])=[O:7].[O:25]1[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=2[NH:28][CH2:27][CH2:26]1>>[O:25]1[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=2[N:28]([CH:11]2[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:8]([C:6](=[O:7])[C:5]3[CH:20]=[CH:21][C:22]([O:23][CH3:24])=[C:3]([O:2][CH3:1])[CH:4]=3)[CH:9]([CH3:19])[CH2:10]2)[CH2:27][CH2:26]1

Participants

3

Reactant 2

HCID 5850963,4-Dihydro-2H-1,4-benzoxazineHCID 69774154cis-1-(3,4-Dimethoxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinol

Product 1

HCID 101144084-(3,4-Dihydro-2H-1,4-benzoxazin-4-yl)-1-(3,4-dimethoxybenzoyl)-2-methyl-1,2,3,4-tetrahydroquinolineYield 59%

Procedure

Starting with cis-1-(3,4-dimethoxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinol (400 mg, 1.22 mmol) prepared in Reference Example 1 and 3,4-dihydro-2H-1,4-benzoxazine (495 mg, 3.66 mmol), the same procedure as shown in Example 1 was repeated to give the titled compound (320 mg, yield: 59%) as a colorless oil. (cis:trans=1:2.3)

Sources & evidence

ORD record
ord-95ff8ff2c845477a98aed329276dcb6d
Source dataset
uspto-grants-2005_08
Patent number
US06930104B2

Reaction notes

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