Isopropylamine → 6,7,8-Trifluoro-1,4-dihydro-1-(1-methylethyl)-4-oxo--quinolinecarboxylic Acid

HRID 980749Notes

Reaction equation

C(N)(C)C.FC1C(F)=C(F)C(F)=CC=1C(=O)C[C:17]([O:19]CC)=[O:18].[F:23][C:24]1[CH:25]=[C:26]2[C:31](=[C:32]([F:35])[C:33]=1[F:34])[N:30]([CH:36]([CH3:38])[CH3:37])[CH:29]=[C:28](C(O)=O)[C:27]2=[O:42]>>[F:23][C:24]1[CH:25]=[C:26]2[C:31](=[C:32]([F:35])[C:33]=1[F:34])[N:30]([CH:36]([CH3:37])[CH3:38])[C:29]([C:17]([OH:19])=[O:18])=[CH:28][C:27]2=[O:42]

Participants

Reactant 3

HCID 6363Isopropylamine

HCID 600916Ethyl 3-oxo-(2,3,4,5-tetrafluorophenyl)propanoate

HCID 134776926,7,8-Trifluoro-1,4-dihydro-1-isopropyl-4-oxoquinoline-3-carboxylic acid

Product 1

HCID 542274906,7,8-Trifluoro-1,4-dihydro-1-(1-methylethyl)-4-oxo--quinolinecarboxylic Acid

Procedure

Using the procedure of Example VV with isopropyl amine, 3.0 g (11.33 mmol) of 2,3,4,5-tetrafluoro-β-oxo-benzeneproprionic acid, ethyl ester was converted to 1.21 g of 6,7,8-trifluoro-1,4-dihydro-1-(1-methylethyl)-4oxo-3-quinolinecarboxylic acid, mp 256°-260° C.

Sources & evidence

ORD record: ord-718f4780e205405fa64940004934e9f3
Source dataset: uspto-grants-1987_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04638067

Reaction notes

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