Sodium Hydroxide → 2-Cyclopentyl-2-(4-(2-quinolylmethoxy)phenyl)acetic acid

HRID 1721682Notes

Reaction equation

C[O:2][C:3](=[O:28])[CH:4]([CH:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1)[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=2)=[CH:7][CH:6]=1.[OH-].[Na+]>CO>[CH:23]1([CH:4]([C:5]2[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]3[CH:22]=[CH:21][C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[N:14]=3)=[CH:7][CH:6]=2)[C:3]([OH:28])=[O:2])[CH2:24][CH2:25][CH2:26][CH2:27]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of the 2-cyclopentyl-2-(4-(2-quinolylmethoxy)phenyl)acetic acid methyl ester prepared in step 1 in methanol (100 ml) was added dropwise 1N sodium hydroxide (25 ml) and the resulting mixture was refluxed at 50° C. for 16 hours. The reaction mixture was then cooled to room temperature, and the methanol was removed in vacuo. The residue was acidified with 10% citric acid and the resulting solid was filtered, washed with water and dried in vacuo to provide 4.8 g of 2-cyclopentyl-2-(4-(2-quinolylmethoxy)phenyl)acetic acid.

Workup

temperatureThe reaction mixture was then cooled to room temperature
customthe methanol was removed in vacuo
filtrationthe resulting solid was filtered
washwashed with water
customdried in vacuo

Sources & evidence

ORD record: ord-c7abd61f625642ec98ba0a2eecca64df
Source dataset: uspto-grants-1996_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05512581

Reaction notes

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