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

HRID 899289Notes

Reaction equation

HRID 899289 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-96b61d3f65b64931be9db8eb6e03d541
Source dataset
uspto-grants-2008_04
Patent number
US07354931B2

Reaction notes

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