Sodium Hydroxide → 1-Ethyl-6-iodo-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid

HRID 1985630Notes

Reaction equation

C([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([I:17])[CH:13]=2)[N:8]([CH2:18][CH3:19])[CH:7]=1)=[O:5])C.[OH-].[Na+]>C1COCC1.O>[CH2:18]([N:8]1[C:9]2[C:14](=[CH:13][C:12]([I:17])=[CH:11][CH:10]=2)[C:15](=[O:16])[C:6]([C:4]([OH:5])=[O:3])=[CH:7]1)[CH3:19]

Participants

Conditions

Temperature: 80 °C

Procedure

1,4-Dihydro-1-ethyl-6-iodo-4-oxo-quinoline-3-carboxylic acid ethyl ester (7.5 g, 0.02 mol) was suspended in THF (75 mL), NaOH (2 equiv.) solution in water (75 mL) was added and the mixture was stirred at 80° C. for 24 hours. After THF was evaporated, the solution was acidified to pH 5 using HCl. The obtained precipitate was filtrated off and dried under reduced pressure yielding the title compound (7.3 g).

Workup

customAfter THF was evaporated
filtrationThe obtained precipitate was filtrated off
customdried under reduced pressure

Sources & evidence

ORD record: ord-9cd744ffd07e4e70842c3402eec267e1
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07547679B2

Reaction notes

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