4-Hydroxybenzaldehyde → HCID 18353282, compound

HRID 429758Notes

Reaction equation

HRID 429758 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[NH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1>C1(C)C=CC=CC=1>[N:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[NH:10][CH2:6][C:5]1[CH:8]=[CH:9][C:2]([OH:1])=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 1264-HydroxybenzaldehydeHCID 104392-Aminopyridine

Product 1

HCID 18353282HCID 18353282, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-Hydroxybenzaldehyde (3.9 g, 32 mmol) and 2-aminopyridine (3.0 g, 32 mmol) were stirred in toluene (100 ml) at room temperature for 5 min. After concentrating in vacuo the residue was dissolved in ethanol (50 ml) and hydrogenated over Pd/C (100 mg) under a hydrogen atmosphere, for 18 h. The reaction mixture was filtered, concentrated and the crude product was chromatographed (dichloromethane-silica) to yield the title compound as white crystals (3.6 g, 56%). 1H NMR (CDCl3) δ 8.10 (1H, m), 7.49 (1H, m), 7.14 (2H, d, J 7.8 Hz), 6.79 (2H, d, J 7.8 Hz), 6.64 (1H, m), 6.47 (1 H, d, J 7.8 Hz), 4.79 (1H, br s) and 4.32 (2H, d, J 5.2 Hz).

Workup

  1. concentrationAfter concentrating in vacuo the residue
  2. dissolutionwas dissolved in ethanol (50 ml) and hydrogenated over Pd/C (100 mg) under a hydrogen atmosphere, for 18 h
  3. filtrationThe reaction mixture was filtered
  4. concentrationconcentrated
  5. customthe crude product was chromatographed (dichloromethane-silica)

Sources & evidence

ORD record
ord-e75934420d9f4e248e7afa0d20886d29
Source dataset
uspto-grants-2001_11
Patent number
US06319922B1

Reaction notes

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