Methylamine → 5-Methyl-6-(methylamino)-2-pyridinemethanol

HRID 376300Notes

Reaction equation

HRID 376300 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][C:3]=1[CH3:10].[CH3:11][NH2:12]>C(O)C>[CH3:10][C:3]1[CH:4]=[CH:5][C:6]([CH2:8][OH:9])=[N:7][C:2]=1[NH:12][CH3:11]

Participants

4

Reactant 2

HCID 6329Methylamine2×HCID 104871386-Chloro-5-methyl-2-pyridinemethanol

Product 1

HCID 107020015-Methyl-6-(methylamino)-2-pyridinemethanolYield 37%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

0.96 g of (6-chloro-5-methylpyridin-2-yl)-methanol (6.09 mmol) and 7 ml of methylamine at 33% in ethanol are heated at 120° C in a bomb for 96 hours. 2 ml of methylamine at 33% in ethanol are added every 24 hours. The reaction mixture is concentrated under vacuum and the title compound isolated by chromatography on a silica column (eluent: cyclohexane/ethyl acetate; 40:60).

Workup

  1. concentrationThe reaction mixture is concentrated under vacuum

Sources & evidence

ORD record
ord-69fdbb6e9d2f48cb995681bbe4f123cd
Source dataset
uspto-grants-2000_02
Patent number
US06020345

Reaction notes

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