Dimethylamine → HCID 86672642, compound

HRID 1530203Notes

Reaction equation

HRID 1530203 reaction equation
BrC[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[C:12]([CH:17]=[C:18]([Cl:20])[N:19]=2)[C:13]([O:15][CH3:16])=[O:14])=[CH:6][CH:5]=1.[CH3:21][NH:22][CH3:23]>C1COCC1>[Cl:20][C:18]1[CH:17]=[C:12]([CH:11]=[C:10]([C:7]2[CH:8]=[CH:9][C:4]([CH2:3][N:22]([CH3:23])[CH3:21])=[CH:5][CH:6]=2)[N:19]=1)[C:13]([O:15][CH3:16])=[O:14]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 131733223HCID 131733223, compound

Product 1

HCID 86672642HCID 86672642, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-(4-(bromoethyl)phenyl)-6-chloroisonicotinate (0.533 g, 1.56 mmol) in THF, dimethylamine (7.8 mL, 2M solution in THF) was added and reaction mass soared 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-ce7279f54a704f90a6c5a8093678a92c
Source dataset
uspto-grants-2015_07
Patent number
US09090562B2

Reaction notes

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