Dimethylamine → Methyl 6-chloro-4-(dimethylamino)nicotinate

HRID 576895Notes

Reaction equation

HRID 576895 reaction equation
[CH3:1][NH:2][CH3:3].Cl[C:5]1[C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][N:8]=[C:7]([Cl:15])[CH:6]=1>CC#N>[Cl:15][C:7]1[CH:6]=[C:5]([N:2]([CH3:3])[CH3:1])[C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][N:8]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 2764083Methyl4,6-dichloronicotinate

Product 1

HCID 71512052Methyl 6-chloro-4-(dimethylamino)nicotinateYield 80.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Dimethylamine (1.23 mL, 9.71 mmol) was slowly added to a stirred solution of methyl 4,6-dichloronicotinate (0.40 g, 1.94 mmol) in MeCN (6 mL) at room temperature. The solution was stirred at room temperature for 18 hours then concentrated in vacuo onto silica gel. Gradient chromatography, eluting with 5% EtOAc:c-Hex over 5 column volume and 5-50% over 15 column volume, gave methyl 6-chloro-4-(dimethylamino)nicotinate (335 mg, 1.56 mmol, 80% yield) as a white solid.

Workup

  1. concentrationthen concentrated in vacuo onto silica gel
  2. washGradient chromatography, eluting with 5% EtOAc

Sources & evidence

ORD record
ord-cc1d2616d8284dbaba506880cee2d225
Source dataset
uspto-grants-2015_05
Patent number
US09040540B2

Reaction notes

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