Sodium Hydroxide → HCID 50992397, compound

HRID 1405509Notes

Reaction equation

HRID 1405509 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][N:2]1[C:11]1[C:12]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[N:13][C:14]2[C:19]([N:20]=1)=[CH:18][C:17]([C:21]([O:23]C)=[O:22])=[CH:16][CH:15]=2.[OH-].[Na+]>CO.O>[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][N:2]1[C:11]1[C:12]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[N:13][C:14]2[C:19]([N:20]=1)=[CH:18][C:17]([C:21]([OH:23])=[O:22])=[CH:16][CH:15]=2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67042131HCID 67042131, compound

Product 1

HCID 50992397HCID 50992397, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Into a 50-mL round-bottom flask, was placed a solution of methyl 3-(3,4-dihydroisoquinolin-2(1H)-yl)-2-phenylquinoxaline-6-carboxylate (110 mg, 0.26 mmol, 1.00 equiv, 95%) in methanol (15 mL). This was followed by the addition of a solution of sodium hydroxide (55.7 mg, 1.39 mmol, 5.00 equiv) in water (1.5 mL) dropwise with stirring. The resulting solution was stirred for overnight at 50° C. in an oil bath. The resulting solution was concentrated under vacuum. The residue was diluted with water. The pH value of the aqueous solution was adjusted to 3-4 with 1N hydrogen chloride. The resulting solids were collected by filtration and washed with methanol. This resulted in 68.1 mg (66%) of 3-(3,4-dihydroisoquinolin-2(1H)-yl)-2-phenylquinoxaline-6-carboxylic acid as a yellow solid.

Workup

  1. customInto a 50-mL round-bottom flask, was placed
  2. stirringThe resulting solution was stirred for overnight at 50° C. in an oil bath
  3. concentrationThe resulting solution was concentrated under vacuum
  4. additionThe residue was diluted with water
  5. filtrationThe resulting solids were collected by filtration
  6. washwashed with methanol
  7. customThis resulted in 68.1 mg (66%) of 3-(3,4-dihydroisoquinolin-2(1H)-yl)-2-phenylquinoxaline-6-carboxylic acid as a yellow solid

Sources & evidence

ORD record
ord-6d465559bb4049c49fb9ac92cf833992
Source dataset
uspto-grants-2014_12
Patent number
US08916560B2

Reaction notes

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