Pyridine → HCID 136335776, compound

HRID 2105129Notes

Reaction equation

HRID 2105129 reaction equation
[NH:1]([C:8]1[N:13]=[C:12]([CH:14]=O)[CH:11]=[CH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:17][OH:18].N1C=CC=CC=1>CCO>[NH:1]([C:8]1[N:13]=[C:12]([CH:14]=[N:17][OH:18])[CH:11]=[CH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 578078012-Anilinopyrimidine-4-carbaldehyde

Product 1

HCID 136335776HCID 136335776, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 2-anilinopyrimidin-4-carbaldehyde (Method 3; 10 g, 50 mmol) and hydroxylamine hydrochloride (17.4 g, 250 mmol) in EtOH (360 ml) and pyridine (17.4 g, 215 mmol) was stirred and heated at reflux for 1 hour. The reaction mixture was allowed to cool and concentrated to about 150 ml total volume by evaporation. Distilled water (600 ml) was added and the precipitated solid collected by filtration, washed thoroughly with distilled water and dried to give the title compound (9.86 g, 92%) as a white solid. NMR: 6.92 (t, 1H), 7.08 (d, 1H), 7.23 (t, 2H), 7.75 (d, 2H), 7.93 (s, 1H), 8.45 (d, 1H), 9.67 (s, 1H), 12.1 (s, 1H); m/z 215.

Workup

  1. temperatureheated
  2. temperatureat reflux for 1 hour
  3. temperatureto cool
  4. concentrationconcentrated to about 150 ml total volume by evaporation
  5. additionDistilled water (600 ml) was added
  6. filtrationthe precipitated solid collected by filtration
  7. washwashed thoroughly with distilled water
  8. customdried

Sources & evidence

ORD record
ord-d292d4ed96034014964be8956fed39a4
Source dataset
uspto-grants-2009_08
Patent number
US07579344B2

Reaction notes

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