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

HRID 395292Notes

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 was cooled to room temperature and the crystalline product was filtered off, washed with cold methanol and dried to give the title compound (7.2 g), yield 77%.

Workup

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

Sources & evidence

ORD record: ord-315d8e0e260942e1aa7550d2fc1a26af
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06605616B1

Reaction notes

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