Potassium Hydroxide → 3-Methyl-6,7-bis(phenylmethoxy)quinoxaline-2-carboxylic acid

HRID 725248Notes

Reaction equation

[CH3:1][C:2]1[C:3]([C:28]([O:30]CC2C=CC=CC=2)=[O:29])=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[C:7]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH:6]=2.[OH-].[K+]>C(O)C.O>[CH3:1][C:2]1[C:3]([C:28]([OH:30])=[O:29])=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([O:12][CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[C:7]([O:20][CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[CH:6]=2

Participants

Conditions

Temperature: 80 °C

Procedure

The compound of Example 27A (4.9 g, 10.0 mmol) was added to a solution of potassium hydroxide (2.2 g, 40.0 mmol) in ethanol/water (80 ml/16 ml) and the mixture was stirred at 80° C. for 20 hours and then cooled (5° C.). The precipitate was collected by suction, washed with ether (4.3 g) and then suspended in water (100 ml). After correction of the pH of this suspension to 2 by the addition of 2N HCl stirring was continued at room temperature for 20 minutes and the crystallized title compound was isolated by suction, washed with water and dried in vacuo over P2O5. Yield: 3.4 g (85%); mp 198°-200° C.

Workup

temperaturecooled (5° C.)
customThe precipitate was collected by suction
washwashed with ether (4.3 g)
additionAfter correction of the pH of this suspension to 2 by the addition of 2N HCl stirring
waitwas continued at room temperature for 20 minutes
customthe crystallized title compound
customwas isolated by suction
washwashed with water
dry with materialdried in vacuo over P2O5

Sources & evidence

ORD record: ord-bb5e63b0a78a4ab1baea0f2e61bd171d
Source dataset: uspto-grants-1998_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05705645

Reaction notes

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