Hydrochloric Acid → HCID 86718113, compound

HRID 2205114Notes

Reaction equation

HRID 2205114 reaction equation
[C:1]([C:3]1[C:4]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:5][C:6]2[C:11]([N:12]=1)=[CH:10][C:9]([C:13]([O:15]C)=[O:14])=[CH:8][CH:7]=2)#N.[OH-].[Na+].Cl>CO.O>[C:4]([C:17]1[CH:22]=[CH:21][C:1]([C:3]2[C:4]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[N:5][C:6]3[C:11]([N:12]=2)=[CH:10][C:9]([C:13]([OH:15])=[O:14])=[CH:8][CH:7]=3)=[CH:19][CH:18]=1)#[N:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86718114HCID 86718114, compound

Product 1

HCID 86718113HCID 86718113, compoundYield 100.5%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A solution of methyl 3-cyano-2-phenylquinoxaline-6-carboxylate (50 mg, 0.17 mmol, 1.00 equiv) and NaOH (16 mg, 0.40 mmol, 3.00 equiv) in MeOH/H2O (5/5 mL) in a 50-mL round-bottom flask was allowed to react, with stirring, for 1 hr at room temperature, followed by a further 1 hr at 50° C. in an oil bath. The reaction progress was monitored by TLC (ethyl acetate:petroleum ether (1:2)). The pH value of the solution was adjusted to 4 with 1N HCl, and the resulting mixture was concentrated under vacuum. The solids were collected by filtration and dried in an oven under reduced pressure, giving 30 mg (46%) of 3-(4-cyanophenyl)-2-phenylquinoxaline-6-carboxylic acid as a white solid.

Workup

  1. customto react
  2. waitfollowed by a further 1 hr at 50° C. in an oil bath
  3. concentrationthe resulting mixture was concentrated under vacuum
  4. filtrationThe solids were collected by filtration
  5. customdried in an oven under reduced pressure

Sources & evidence

ORD record
ord-1f411363a6a5470596916f881e0a5e56
Source dataset
uspto-grants-2016_06
Patent number
US09370522B2

Reaction notes

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