Hydrochloric Acid → HCID 50992395, compound

HRID 1405505Notes

Reaction equation

HRID 1405505 reaction equation
[CH2:1]([N:3]([CH2:24][CH3:25])[C:4]1[C:5]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[N:6][C:7]2[C:12]([N:13]=1)=[CH:11][C:10]([C:14]([O:16]C)=[O:15])=[CH:9][CH:8]=2)[CH3:2].[OH-].[Na+].Cl>CO.O>[CH2:24]([N:3]([CH2:1][CH3:2])[C:4]1[C:5]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[N:6][C:7]2[C:12]([N:13]=1)=[CH:11][C:10]([C:14]([OH:16])=[O:15])=[CH:9][CH:8]=2)[CH3:25]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67041743HCID 67041743, compound

Product 1

HCID 50992395HCID 50992395, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Into a 50-mL round-bottom flask, was placed a solution of methyl 3-(diethylamino)-2-phenylquinoxaline-6-carboxylate (117 mg, 0.35 mmol, 1.00 equiv) in methanol (15 mL). This was followed by the addition of a solution of sodium hydroxide (69.9 mg, 1.75 mmol, 5.00 equiv) in water (2 mL) dropwise with stirring. The resulting solution was stirred overnight at 50° C. in an oil bath. The pH value of the solution was adjusted to 3-4 with 1N hydrogen chloride. The resulting mixture was concentrated under vacuum. The crude product (110 mg) was purified by Prep-HPLC with the following conditions: Column, SunFire Prep C18, 5 um, 19*150 mm; mobile phase, water with 0.05% TFA and methanol (70% methanol up to 90% in 10 min); Detector, UV 254 nm. This resulted in 70 mg (62%) of 3-(diethylamino)-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 overnight at 50° C. in an oil bath
  3. concentrationThe resulting mixture was concentrated under vacuum
  4. customThe crude product (110 mg) was purified by Prep-HPLC with the following conditions
  5. customThis resulted in 70 mg (62%) of 3-(diethylamino)-2-phenylquinoxaline-6-carboxylic acid as a yellow solid

Sources & evidence

ORD record
ord-9b67fa71e3624497bf2273e002540ced
Source dataset
uspto-grants-2014_12
Patent number
US08916560B2

Reaction notes

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