Hydrochloric Acid → 3-Methoxycarbonylmethyl-2-oxo-1,2,3,4-tetrahydro-quinolin-7-carboxylic Acid

HRID 2302006Notes

Reaction equation

C([O:5][C:6]([C:8]1[CH:17]=[C:16]2[C:11]([CH2:12][CH:13]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[C:14](=[O:18])[NH:15]2)=[CH:10][CH:9]=1)=[O:7])(C)(C)C.Cl>O1CCOCC1>[CH3:23][O:22][C:20]([CH2:19][CH:13]1[CH2:12][C:11]2[C:16](=[CH:17][C:8]([C:6]([OH:7])=[O:5])=[CH:9][CH:10]=2)[NH:15][C:14]1=[O:18])=[O:21]

Participants

Conditions

Temperature: 45 °C

Procedure

A suspension of 3-methoxycarbonylmethyl-2-oxo-1,2,3,4-tetrahydro-quinoline-7-carboxylic acid tert-butyl ester (3.5 g, 13.2 mmol) in dioxane (40 mL) was treated with 10 mL of 4N hydrochloric acid in dioxane and heated to 40-50° C. Evaporation of the volatiles in vacuo gave the title compound (3.35 g, 97%). NMR (dmso-d6, 200 MHz) : δ2.7-3.4 (m, 5H, CH2CHCH2), 3.6 (s, 3H, CH3), 7.2-7.5 (m, 3H, ArH), 10.3 (s, 1 H, NH).

Workup

customEvaporation of the volatiles in vacuo

Sources & evidence

ORD record: ord-5665534271d242be9b434914317578fb
Source dataset: uspto-grants-2002_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06429214B1

Reaction notes

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