Sodium Hydroxide → HCID 86718146, compound

HRID 2205162Notes

Reaction equation

HRID 2205162 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:18]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)=[N:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14](/[CH:27]=[CH:28]/[C:29]([O:31]C)=[O:30])[CH:15]=3)[N:10]=2)=[CH:5][CH:4]=1.[OH-].[Na+]>CO.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:18]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)=[N:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14](/[CH:27]=[CH:28]/[C:29]([OH:31])=[O:30])[CH:15]=3)[N:10]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86718145HCID 86718145, compound

Product 1

HCID 86718146HCID 86718146, compoundYield 55.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of (E)-methyl 3-(2,3-bis(4-methoxyphenyl)quinoxalin-6-yl)acrylate (150 mg, 0.35 mmol, 1.00 equiv) and sodium hydroxide (70.4 mg, 1.76 mmol, 5.00 equiv) in methanol (10 mL) and H2O (2 ml) was stirred for 2 h at 50° C. in an oil bath. The resulting mixture was concentrated under vacuum, diluted with 20 mL of water. The pH value of the solution was adjusted to 3 with 1N hydrochloric acid. The solids were collected by filtration, and purified by re-crystallization from methanol, affording 80 mg (55%) of (E)-3-(2,3-bis(4-methoxyphenyl)quinoxalin-6-yl)acrylic acid as a yellow solid.

Workup

  1. concentrationThe resulting mixture was concentrated under vacuum
  2. additiondiluted with 20 mL of water
  3. filtrationThe solids were collected by filtration
  4. custompurified by re-crystallization from methanol

Sources & evidence

ORD record
ord-36d00026b8fb45b4afbbac8be04e8232
Source dataset
uspto-grants-2016_06
Patent number
US09370522B2

Reaction notes

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