4-Hydroxyphenylpyruvic Acid → HCID 22724147, compound

HRID 2231050Notes

Reaction equation

HRID 2231050 reaction equation
[NH2:1][C:2]1[C:3]([NH:8][C:9]2[CH:10]=[C:11]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:12]=[CH:13][CH:14]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.[OH:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29](=O)[C:30](O)=[O:31])=[CH:24][CH:23]=1.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>C(O)C>[C:11]1([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:12]=[CH:13][CH:14]=[C:9]([N:8]2[C:30](=[O:31])[C:29]([CH2:28][C:25]3[CH:24]=[CH:23][C:22]([OH:21])=[CH:27][CH:26]=3)=[N:1][C:2]3[CH:7]=[CH:6][CH:5]=[N:4][C:3]2=3)[CH:10]=1

Participants

6

Reactant 4

HCID 9794-Hydroxyphenylpyruvic AcidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 22724036HCID 22724036, compound

Product 1

HCID 22724147HCID 22724147, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-amino-2-(3-biphenylylamino)pyridine (196 mg) and 3-(4-hydroxyphenyl)pyruvic acid (162 mg) in ethanol (5 ml) was stirred under reflux for 2 hours. The mixture was cooled and then poured into a mixture of ethyl acetate and aqueous sodium bicarbonate. The organic phase was separated, washed with aqueous sodium bicarbonate and brine, dried over magnesium sulfate and concentrated. The residue was crystallized from methanol to give 4-(3-biphenylyl)-2-(4-hydroxybenzyl)-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine (186 mg).

Workup

  1. temperatureunder reflux for 2 hours
  2. temperatureThe mixture was cooled
  3. customThe organic phase was separated
  4. washwashed with aqueous sodium bicarbonate and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was crystallized from methanol

Sources & evidence

ORD record
ord-386a909779c5454097a4f1ab61e05fcc
Source dataset
uspto-grants-2002_07
Patent number
US06426345B1

Reaction notes

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