Acetic Acid → (2-Chloro-5-methyl-pyridin-3-ylmethyl)-ethyl-amine

HRID 389265Notes

Reaction equation

HRID 389265 reaction equation
[Cl:1][C:2]1[C:7]([CH:8]=O)=[CH:6][C:5]([CH3:10])=[CH:4][N:3]=1.[CH2:11]([NH2:13])[CH3:12].C([BH3-])#N.[Na+].C(O)(=O)C>CO>[Cl:1][C:2]1[C:7]([CH2:8][NH:13][CH2:11][CH3:12])=[CH:6][C:5]([CH3:10])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6341EthylamineHCID 5003444Sodium cyanoborohydrideHCID 98340182-Chloro-5-methylpyridine-3-carbaldehyde

Product 1

HCID 58579979(2-Chloro-5-methyl-pyridin-3-ylmethyl)-ethyl-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Chloro-5-methyl-pyridine-3-carbaldehyde (0.22 g, 1.41 mmol), ethylamine (2M in THF; 1.06 mL, 2.12 mmol), and sodium cyanoborohydride (0.133 g, 2.12 mmol) were combined in MeOH (2.52 mL). Acetic acid (0.12 mL, 2.12 mmol) was added, and the reaction was stirred at room temperature for 1 hour. The mixture was concentrated, and the residue was dissolved in CH2Cl2, washed with saturated aqueous NaHCO3, concentrated, and purified by silica gel chromatography (0-10% MeOH in CH2Cl2) to give the title compound.

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionthe residue was dissolved in CH2Cl2
  3. washwashed with saturated aqueous NaHCO3
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography (0-10% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-77df177e3b63493e8d4777d41fe8cd97
Source dataset
uspto-grants-2013_02
Patent number
US08378107B2

Reaction notes

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