Hydrochloric Acid → (E,E,E)-7-[1-(1-Methylethyl)-1,2,3,4-tetrahydroquinolin-6-yl]-3-methyl-octa-2,4,6-trienoic acid

HRID 2229172Notes

Reaction equation

[CH3:1][CH:2]([N:4]1[C:13]2[C:8](=[CH:9][C:10](/[C:14](/[CH3:25])=[CH:15]/[CH:16]=[CH:17]/[C:18](/[CH3:24])=[CH:19]/[C:20]([O:22]C)=[O:21])=[CH:11][CH:12]=2)[CH2:7][CH2:6][CH2:5]1)[CH3:3].[OH-].[Na+].Cl>C(O)C>[CH3:3][CH:2]([N:4]1[C:13]2[C:8](=[CH:9][C:10](/[C:14](/[CH3:25])=[CH:15]/[CH:16]=[CH:17]/[C:18](/[CH3:24])=[CH:19]/[C:20]([OH:22])=[O:21])=[CH:11][CH:12]=2)[CH2:7][CH2:6][CH2:5]1)[CH3:1]

Participants

Conditions

Temperature: 60 °C

Procedure

330 mg of methyl (E,E,E)-7-[1-(1-methylethyl)-1,2,3,4-tetrahydroquinolin-6-yl]-3-methylocta-2,4,6-trienoate was dissolved in 10 ml of ethanol, followed by the addition of 1.0 ml of a 5N aqueous solution of sodium hydroxide. The obtained mixture was heated at 60° C. for one hour and adjusted to pH5 by adding 6N hydrochloric acid under cooling with ice. The crystals thus precipitated were recovered by filtration and recrystallized from ethanol to give 100 mg of the title compound as orange crystals.

Workup

temperatureunder cooling with ice
customThe crystals thus precipitated
filtrationwere recovered by filtration
customrecrystallized from ethanol

Sources & evidence

ORD record: ord-bd3a0c3728a14d1ca6c9b8fb6b89a1b9
Source dataset: uspto-grants-2002_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06420363B1

Reaction notes

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