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

HRID 1477359Notes

Reaction equation

HRID 1477359 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-f0df36e7d9b4496989a2d1aef5a38dba
Source dataset
uspto-grants-2016_08
Patent number
US09403797B2

Reaction notes

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