Potassium Hydroxide → HCID 86280323, compound

HRID 525973Notes

Reaction equation

[Cl:1][C:2]1[C:11]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[C:10]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)[CH:9]=[C:8]2[C:3]=1[C:4](=[O:47])[C:5]([C:35]([O:37]CC1C=CC(OC)=CC=1)=[O:36])=[CH:6][N:7]2[CH:32]1[CH2:34][CH2:33]1.[OH-].[K+]>CO.O>[Cl:1][C:2]1[C:11]([O:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)=[C:10]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)[CH:9]=[C:8]2[C:3]=1[C:4](=[O:47])[C:5]([C:35]([OH:37])=[O:36])=[CH:6][N:7]2[CH:32]1[CH2:33][CH2:34]1

Participants

Conditions

Temperature: 90 °C

Procedure

To a suspension of 4-methoxybenzyl 5-chloro-1-cyclopropyl-6,7-bis((4-methoxy benzyl)oxy)-4-oxo-1,4-dihydroquinoline-3-carboxylate (18 g, 27.4 mmol) in a mixture of Methanol (120 mL) and Water (60.0 mL) was added potassium hydroxide (3.08 g, 54.9 mmol) portionwise. The resulting mixture was stirred at 90° C. for 3 h. LCMS indicated completion of the reaction. The reaction mixture was cooled down to r.t. and concentrated, and was then diluted with water and adjusted pH to 1 using 2 N HCl (aq.). The precipitates were collected by filtration and dried to afford 5-chloro-1-cyclopropyl-6,7-bis((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (12.6 g, 23.51 mmol, 86% yield) as pale yellow solid. LCMS: [M+H]+: 536.3.

Workup

customcompletion of the reaction
temperatureThe reaction mixture was cooled down to r.t.
concentrationconcentrated
additionwas then diluted with water and adjusted pH to 1 using 2 N HCl (aq.)
filtrationThe precipitates were collected by filtration
customdried

Sources & evidence

ORD record: ord-d39938e71864406ea9ce0155c7c13f9e
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340556B2

Reaction notes

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