Hydrochloric Acid → 3-Quinolinecarboxylic acid, 1,2-dihydro-4-hydroxy-5-methoxy-1-methyl-2-oxo-

HRID 1357643Notes

Reaction equation

Cl.C([O:4][C:5]([C:7]1[C:8](=[O:21])[N:9]([CH3:20])[C:10]2[C:15]([C:16]=1[OH:17])=[C:14]([O:18][CH3:19])[CH:13]=[CH:12][CH:11]=2)=[O:6])C>C(OC(=O)C)(=O)C>[OH:17][C:16]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[O:18][CH3:19])[N:9]([CH3:20])[C:8](=[O:21])[C:7]=1[C:5]([OH:6])=[O:4]

Participants

Conditions

Temperature: 80 °C

Procedure

While cooling, 10 ml of conc. hydrochloric acid was added to 30 ml of acetic anhydride. To this solution, 1,2-dihydro-4-hydroxy-5-methoxy-1-methyl-2-oxo-quinoline-3-carboxylic acid ethyl ester (10.5 g, 38 mmol) was added and the mixture heated at 80° C. for 14 hours. The mixture cooled to room temperature and the crystalline product was filtered off, washed with cold methanol and dried to yield the title compound (7.2 g), yield 77%.

Workup

temperatureWhile cooling
temperatureThe mixture cooled to room temperature
filtrationthe crystalline product was filtered off
washwashed with cold methanol
customdried

Sources & evidence

ORD record: ord-2a4f710578c748ef8ea94aaae84a98f8
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06593343B2

Reaction notes

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