Hydrochloric Acid → HCID 19081730, compound

HRID 963388Notes

Reaction equation

HRID 963388 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:32])=[C:11]([C:14]4[CH:19]=[C:18]([CH:20]5OCC(C)(C)C[O:21]5)[CH:17]=[C:16]([O:28][CH3:29])[C:15]=4[O:30][CH3:31])[CH:12]=3)[C:7](=[O:33])[C:6]([C:34]([O:36]CC)=[O:35])=[CH:5]2)[CH2:3][CH2:2]1.Cl>C(O)C>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:32])=[C:11]([C:14]4[CH:19]=[C:18]([CH:20]=[O:21])[CH:17]=[C:16]([O:28][CH3:29])[C:15]=4[O:30][CH3:31])[CH:12]=3)[C:7](=[O:33])[C:6]([C:34]([OH:36])=[O:35])=[CH:5]2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 19081600HCID 19081600, compound

Product 1

HCID 19081730HCID 19081730, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

575 mg of ethyl 1-cyclopropyl-7-[5-(5,5-dimethyl-1,3-dioxan-2-yl)-2,3-dimethoxy-phenyl]-6-fluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylate (Example 7a)) are heated to boiling under reflux in a mixture of 8 ml of a 2N aqueous hydrochloric acid solution and 5 ml of ethanol for 6 hrs. The reaction mixture is cooled in an ice bath and the separated precipitate is filtered off under suction and washed with 20 ml of water and with 50 ml of ether. 330 mg (73%) of 1-cyclopropyl-6-fluoro-7-(5-formyl-2,3-dimethoxy-phenyl)-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid are obtained as a colourless solid. M.p.>230°. Mass spectrum: peaks: inter alia at 411 (M+, 6%), 367 (100%), 338 (6%), 202 (8%), 184 (10%).

Workup

  1. temperatureThe reaction mixture is cooled in an ice bath
  2. filtrationthe separated precipitate is filtered off under suction
  3. washwashed with 20 ml of water and with 50 ml of ether

Sources & evidence

ORD record
ord-233bcf8da9354b9fada9b54628a2781b
Source dataset
uspto-grants-1998_06
Patent number
US05763450

Reaction notes

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