Dimethylamine → 5-Bromo-4-(dimethylamino)-2-pyridinemethanol

HRID 1655223Notes

Reaction equation

HRID 1655223 reaction equation
[CH3:1][NH:2][CH3:3].N1CCOCC1.Cl[C:11]1[C:16]([Br:17])=[CH:15][N:14]=[C:13]([CH2:18][OH:19])[CH:12]=1.ClC1C(CO)=NC=CC=1Cl>C(O)C>[CH3:1][N:2]([CH3:3])[C:11]1[C:16]([Br:17])=[CH:15][N:14]=[C:13]([CH2:18][OH:19])[CH:12]=1

Participants

6

Reactant 4

HCID 674DimethylamineHCID 8083MorpholineHCID 19791171(5-Bromo-4-chloropyridin-2-yl)methanolHCID 221173013,4-Dichloro-2-(hydroxymethyl)pyridine

Product 1

HCID 197911255-Bromo-4-(dimethylamino)-2-pyridinemethanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Substituting 33% w/w dimethylamine in ethanol (15 ml) for morpholine and 4-chloro-5-bromo-2-hydroxymethylpyridine (5 g) for 3,4-dichloro-2-hydroxymethylpyridine and using corresponding molar proportions of the other reagents in the method of Example 3D gave after chromatography (silica, chloroform:methanol, 98:2) 4-dimethylamino-5-bromo-2-hydroxymethylpyridine, 3.62 g, as an oil.

Sources & evidence

ORD record
ord-8bf392fa9be344bf8e1bda0a59135b1c
Source dataset
uspto-grants-1993_10
Patent number
US05250527

Reaction notes

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