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 378382Notes

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-c9b1a470abac41cd977d66d4f6c590f2
Source dataset: uspto-grants-2000_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06030964

Reaction notes

Loading…