Ethyl Acetate → HCID 22724378, compound

HRID 2086885Notes

Reaction equation

HRID 2086885 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.[N+:21]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH2:30][C:31](=O)[C:32](O)=[O:33])([O-:23])=[O:22].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:32](=[O:33])[C:31]([CH2:30][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=3[N+:21]([O-:23])=[O:22])=[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 8857Ethyl AcetateHCID 795833-(2-Nitrophenyl)-2-oxopropanoic acidHCID 516892Sodium BicarbonateHCID 22724036HCID 22724036, compound

Product 1

HCID 22724378HCID 22724378, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-amino-2-(3-biphenylylamino)pyridine (196 mg) and 3-(2-nitrophenyl)pyruvic acid (188 mg) in ethanol (5 ml) was stirred under reflux for 1 hour. 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-(2-nitrobenzyl)-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine (140 mg).

Workup

  1. temperatureunder reflux for 1 hour
  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-1cf34cded95c4bcf84e955375d4d8cd6
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

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