3-Methoxybenzoic Acid → 1-(3-Methoxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinol

HRID 585364

Reaction equation

HRID 585364 reaction equation
[CH3:1][CH:2]1[CH2:11][CH:10]([OH:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=1)[C:18](O)=[O:19]>>[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=1)[C:18]([N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:10]([OH:12])[CH2:11][CH:2]1[CH3:1])=[O:19]

Participants

3

Reactant 2

HCID 114613-Methoxybenzoic AcidHCID 1476341,2,3,4-Tetrahydro-2-methyl-4-quinolinol

Product 1

HCID 223392321-(3-Methoxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinolYield 27%

Procedure

Starting with 2-methyl-1,2,3,4-tetrahydro-4-quinolinol (3.00 g, 18.3 mmol) synthesized in the published manner and 3-methoxybenzoic acid (3.34 g, 22.0 mmol), the same procedure as shown in Reference Example 19 was repeated to give the titled compound (1.45 g, yield: 27%) as a white crystal. (cis:trans=1:1)

Sources & evidence

ORD record
ord-5b593778956443bd8eafd7c9b3e79dea
Source dataset
uspto-grants-2005_08
Patent number
US06930104B2

Linked notes

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