Water → HCID 178443613, compound

HRID 928888Notes

Reaction equation

HRID 928888 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=O.[C:9]([NH2:17])([CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:11])[CH3:10].O>C(Cl)Cl>[CH3:10][C:9](/[N:17]=[CH:7]/[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)([CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:11]

Participants

5

Reactant 3

HCID 962WaterHCID 142732-PyridinecarboxaldehydeHCID 61017tert-Octylamine

Product 1

HCID 178443613HCID 178443613, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In air, to a solution of 2-pyridinecarboxaldehyde (0.338 g, 0.300 mL, 3.15 mmol, 1.01 equiv) in CH2Cl2 (10 mL) was added tert-octylamine (0.402 g, 0.500 mL, 3.11 mmol, 1.00 equiv). After heating at reflux for 1.5 h with azeotropic removal of water using a Dean-Stark trap, the reaction mixture was concentrated under reduced pressure. The residue was purified by bulb-to-bulb distillation (250 mTorr, 140° C.) to give the title compound as a colorless oil (0.639 g, 94% yield).

Workup

  1. temperatureAfter heating
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. distillationThe residue was purified by bulb-to-bulb distillation (250 mTorr, 140° C.)

Sources & evidence

ORD record
ord-ed2545d7c770491a8b402bf2c4065a3a
Source dataset
uspto-grants-2016_03
Patent number
US09290591B2

Reaction notes

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