Trifluoroacetic acid → 4-[3-(4,4-Dimethyl-1,2,3,4-tetrahydro-quinolin-7-yl)-oct-1-enyl]-benzoic acid methyl ester

HRID 2415201Notes

Reaction equation

HRID 2415201 reaction equation
C(OC([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH:18]([CH:24]=[CH:25][C:26]3[CH:31]=[CH:30][C:29]([C:32]([O:34][CH3:35])=[O:33])=[CH:28][CH:27]=3)[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH:16]=2)[C:11]([CH3:37])([CH3:36])[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH3:35][O:34][C:32](=[O:33])[C:29]1[CH:28]=[CH:27][C:26]([CH:25]=[CH:24][CH:18]([C:15]2[CH:16]=[C:17]3[C:12]([C:11]([CH3:37])([CH3:36])[CH2:10][CH2:9][NH:8]3)=[CH:13][CH:14]=2)[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 692180957-{1-[2-(4-methoxycarbonyl-phenyl)-vinyl]-hexyl}-4,4-dimethyl-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester

Product 1

HCID 692164454-[3-(4,4-Dimethyl-1,2,3,4-tetrahydro-quinolin-7-yl)-oct-1-enyl]-benzoic acid methyl esterYield 91.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 7-{1-[2-(4-methoxycarbonyl-phenyl)-vinyl]-hexyl}-4,4-dimethyl-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester (0.98 g) in 10 mL of dichloromethane was treated with 1.5 mL of trifluoroacetic acid. The mixture was stirred at room temperature for four hours and then was concentrated in vacuo to yield 0.72 g of 4-[3-(4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-7-yl)-oct-1-enyl]-benzoic acid methyl ester as a yellow oil.

Workup

  1. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-7ed05faada2a4fc0890118ff2c9251d8
Source dataset
uspto-grants-2004_11
Patent number
US06818652B2

Reaction notes

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