Ethyl 7-bromoacetyl-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3quinolinecarboxylate → Ethyl 6-fluoro-4-hydroxyquinoline-3-carboxylate

HRID 622497Notes

Reaction equation

HRID 622497 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][C:11](C(=O)CBr)=[C:12]([F:17])[CH:13]=2)[N:8](CC)[CH:7]=1)=[O:5])[CH3:2].C(N(CC(N)=S)CC)(=O)C>C(O)C>[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([F:17])[CH:13]=2)[NH:8][CH:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 13853634Ethyl 7-bromoacetyl-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3quinolinecarboxylateHCID 140236322-(N-acetyl-N-ethylamino)thioacetamide

Product 1

HCID 710779Ethyl 6-fluoro-4-hydroxyquinoline-3-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

According to example 30, reacting 7-bromoacetyl-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid ethyl ester with 2-(N-acetyl-N-ethylamino)thioacetamide in ethanol gave 1-ethyl-7-2-[(N-acetyl-N-ethylamino)methyl]-4-thiazolyl]-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid ethyl ester, mp 160°-161° C. which was then hydrolyzed in refluxing 6N hydrochloric acid to afford the title compound, mp 289°-300° C. (dec).

Sources & evidence

ORD record
ord-791852a944394ac897f0dde5ce947f3b
Source dataset
uspto-grants-1988_09
Patent number
US04771054

Reaction notes

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