Sodium Hydroxide → HCID 86718137, compound

HRID 2205151Notes

Reaction equation

[OH-].[Na+].[C:3]([C:6]1[CH:7]=[C:8]([C:12]2[C:13]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[N:14][C:15]3[C:20]([N:21]=2)=[CH:19][C:18]([C:22]([O:24]C)=[O:23])=[CH:17][CH:16]=3)[CH:9]=[CH:10][CH:11]=1)([OH:5])=[O:4]>O.CO>[C:3]([C:6]1[CH:7]=[C:8]([C:12]2[C:13]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[N:14][C:15]3[C:20]([N:21]=2)=[CH:19][C:18]([C:22]([OH:24])=[O:23])=[CH:17][CH:16]=3)[CH:9]=[CH:10][CH:11]=1)([OH:5])=[O:4]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of NaOH (68.7 mg, 1.72 mmol, 5.00 equiv) in water (3 mL) was added dropwise with stirring to a solution of methyl 3-(3-carboxyphenyl)-2-phenylquinoxaline-6-carboxylate (131.9 mg, 0.33 mmol, 1.00 equiv. in methanol (10 mL). The resulting solution was stirred overnight at 50° C. in an oil bath. The mixture was concentrated by vacuum; the pH was adjusted to 3-4 with 1N hydrochloric acid, the solid precipitate was filtered and washed with ether, affording 60 mg (49%) of 3-(3-carboxyphenyl)-2-phenylquinoxaline-6-carboxylic acid as a white solid.

Workup

concentrationThe mixture was concentrated by vacuum
filtrationthe solid precipitate was filtered
washwashed with ether

Sources & evidence

ORD record: ord-b31fa0b7332a43d0a134ab9ad4adf95b
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09370522B2

Reaction notes

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