Dimethylamine → HCID 86672642, compound

HRID 1959173Notes

Reaction equation

HRID 1959173 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]([CH:16]=[C:17]([Cl:19])[N:18]=2)[C:12]([O:14][CH3:15])=[O:13])=[CH:5][CH:4]=1.[CH3:20][NH:21][CH3:22]>C1COCC1>[Cl:19][C:17]1[CH:16]=[C:11]([CH:10]=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([CH2:2][N:21]([CH3:22])[CH3:20])=[CH:4][CH:5]=2)[N:18]=1)[C:12]([O:14][CH3:15])=[O:13]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 86672640HCID 86672640, compound

Product 1

HCID 86672642HCID 86672642, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-(4-(bromomethyl)phenyl)-6-chloroisonicotinate (0.533 g, 1.56 mmol) in THF, dimethylamine (7.8 mL, 2M solution in THF) was added and reaction mass stirred at rt for overnight. On completion, reaction mass concentrated and crude obtained was purified by column chromatography over silica gel obtaining pure methyl 2-chloro-6-(4-((dimethylamino)methyl)phenyl)isonicotinate (0.48 g, 99%).

Workup

  1. customreaction mass
  2. customOn completion, reaction mass
  3. concentrationconcentrated
  4. customcrude obtained
  5. customwas purified by column chromatography over silica gel obtaining pure methyl 2-chloro-6-(4-((dimethylamino)methyl)phenyl)isonicotinate (0.48 g, 99%)

Sources & evidence

ORD record
ord-b269e0c11e8a4cd9916b34947c9cc5b0
Source dataset
uspto-grants-2013_04
Patent number
US08410088B2

Reaction notes

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