Sodium Hydroxide → 1-Ethyl-4,5-dioxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylic acid

HRID 444201Notes

Reaction equation

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

Participants

Conditions

Temperature: 90 °C

Procedure

Sodium hydroxide (1.6 g) was dissolved in 30 ml of water, and 2 g of ethyl 1-ethyl-4,5-dioxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate was added, and the mixture was stirred at 90° C. for 2 hours. The insoluble matter was removed, and the filtrate was adjusted to pH 1 with dilute hydrochloric acid under ice cooling. The crystals that precipitated were collected by filtration to afford 0.72 g of the captioned product. The product had a melting point of 212° to 214° C. (uncorrected). The infrared absorption spectrum (KBr tablet method) of the product had maximum absorptions at 3460, 2960, 1740, 1710, 1640 and 1495 cm-1. The nuclear magnetic resonance spectrum (CF3COOH, 60 Mc, TMS) had signals at δ1.70 (3H, t, J=7.5 Hz), 2.2-2.75 (2H, m), 2.8-3.2 (2H, m), 3.3-3.65 (2H, m), 4.64 (2H, q, J=7.5 Hz) and 9.30 (1H, s).

Workup

customThe insoluble matter was removed
customThe crystals that precipitated
filtrationwere collected by filtration

Sources & evidence

ORD record: ord-c51c5db44ff943bb9c3b7903a597e610
Source dataset: uspto-grants-1981_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04263302

Reaction notes

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