6-Methyl-2-pyridinecarboxaldehyde → HCID 86743636, compound

HRID 329421Notes

Reaction equation

HRID 329421 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([CH:8]=O)[CH:5]=[CH:4][CH:3]=1.[CH:10]([C:12]1[CH:17]=[CH:16][C:15]([C@H:18]([NH2:20])[CH3:19])=[CH:14][CH:13]=1)=[CH2:11]>C(O)C>[CH:10]([C:12]1[CH:17]=[CH:16][C:15]([C@H:18]([N:20]=[CH:8][C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=2)[CH3:19])=[CH:14][CH:13]=1)=[CH2:11]

Participants

4

Reactant 2

HCID 707376-Methyl-2-pyridinecarboxaldehydeHCID 51358468HCID 51358468, compound

Product 1

HCID 86743636HCID 86743636, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1.69 g (13.9 mmol) of 6-methylpyridine-2-carbaldehyde, 2.05 g (13.9 mmol) of (R)-1-(4-vinylphenyl)-ethylamine and 25 ml of ethanol is heated under reflux for 1 hour. The solvent is then distilled off under about 3 kPa, and the residue is distilled in a bulb tube furnace at 170° C. and under 0.11 Pa. 3.3 g (88% of theory) of an oil are obtained, which crystallises at room temperature. Melting point: about 25° C., [α]D20 =21.6° (c=1.036, chloroform). Elemental analysis: Found: C 81.71; H 7.25; N 11.02%; Calculated for C17H18N2 (250.35): C 81.56; H 7.25; N 11.19%.

Workup

  1. temperatureunder reflux for 1 hour
  2. distillationThe solvent is then distilled off under about 3 kPa
  3. distillationthe residue is distilled in a bulb tube furnace at 170° C.
  4. custom3.3 g (88% of theory) of an oil are obtained
  5. customwhich crystallises at room temperature
  6. customMelting point: about 25° C., [α]D20 =21.6° (c=1.036, chloroform)

Sources & evidence

ORD record
ord-a8747f72dc4d40ee8308b0bb8789d9a7
Source dataset
uspto-grants-1990_01
Patent number
US04891412

Reaction notes

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