Indoline → 4-(2,3-dihydro-1H-indol-1-yl)-1-(3,4-dimethoxybenzoyl)-1,2,3,4-tetrahydroquinoline

HRID 585357Notes

Reaction equation

HRID 585357 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[C:6]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11](O)[CH2:10][CH2:9]1)=[O:7].[NH:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:26][CH2:25]1>>[N:24]1([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:19]=[CH:20][C:21]([O:22][CH3:23])=[C:3]([O:2][CH3:1])[CH:4]=3)[CH2:9][CH2:10]2)[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:26][CH2:25]1

Participants

3

Reactant 2

HCID 10328IndolineHCID 223392201-(3,4-Dimethoxybenzoyl)-1,2,3,4-tetrahydro-4-quinolinol

Product 1

HCID 223392704-(2,3-dihydro-1H-indol-1-yl)-1-(3,4-dimethoxybenzoyl)-1,2,3,4-tetrahydroquinolineYield 54.3%

Procedure

Starting with 1-(3,4-dimethoxybenzoyl)-1,2,3,4-tetrahydro-4-quinolinol (390 mg, 1.19 mmol) prepared in Reference Example 2 and indoline (425 mg, 3.57 mmol), the same procedure as shown in Example 1 was repeated to give the product of interest, i.e., 4-(2,3-dihydro-1H-indol-1-yl)-1-(3,4-dimethoxybenzoyl)-1,2,3,4-tetrahydroquinoline (268 mg, yield: 54%) as a white crystal.

Sources & evidence

ORD record
ord-4b7464675c6d4b4ba6d380ded48d5c05
Source dataset
uspto-grants-2005_08
Patent number
US06930104B2

Reaction notes

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