Methyl p-toluenesulfonate → HCID 86744276, compound

HRID 2081515Notes

Reaction equation

HRID 2081515 reaction equation
[F:1][C:2]1([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[C:10]([CH2:18][OH:19])[N:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH2:3]1.[C:20]1([CH3:31])[CH:25]=[CH:24][C:23]([S:26]([O:29]C)(=[O:28])=[O:27])=[CH:22][CH:21]=1>>[C:20]1([CH3:31])[CH:21]=[CH:22][C:23]([S:26]([O-:29])(=[O:27])=[O:28])=[CH:24][CH:25]=1.[F:1][C:2]1([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[C:10]([CH2:18][OH:19])[N+:9]=2[CH3:20])[CH:3]=[CH:4][CH:5]=[CH:6][CH2:7]1

Participants

3

Reactant 2

HCID 6645Methyl p-toluenesulfonateHCID 67858434HCID 67858434, compound

Product 1

HCID 86744276HCID 86744276, compoundYield 145.1%

Procedure

1-(1-Fluorophenyl)-3-isoquinolinecarboxylic acid was converted into its ethylester and then reduced using lithium aluminum hydride to obtain 1-(1-fluorophenyl)-3-isoquinolinemethanol. 1.26 g of the obtained 1-(1-fluorophenyl)-3-isoquinolinemethanol was reacted with 930 mg of methyl p-toluenesulfonate in the same manner as in Reference Example 10 to give 1.6 g of the desired compound as a pale orange-colored solid.

Sources & evidence

ORD record
ord-5b2fd29590e04940a69512dce5655218
Source dataset
uspto-grants-1993_02
Patent number
US05183811

Reaction notes

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