6-Chloro-N-methoxy-N-methylnicotinamide → HCID 80461104, compound

HRID 1669267Notes

Reaction equation

HRID 1669267 reaction equation
[Cl:1][C:2]1[CH:13]=[CH:12][C:5]([C:6](N(OC)C)=[O:7])=[CH:4][N:3]=1>O1CCCC1>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C:6](=[O:7])[CH2:4][CH2:5][CH2:12][CH2:13][CH3:2])=[CH:12][CH:13]=1

Participants

3

Reactant 1

HCID 114355976-Chloro-N-methoxy-N-methylnicotinamide

Product 1

HCID 80461104HCID 80461104, compoundYield 160.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

6-Chloro-N-methoxy-N-methyl-nicotinamide (6.20 g, 30.90 mmol) is suspended in anhydrous tetrahydrofuran (200 mL), and cooled to 0° C. with stirring under nitrogen. N-pentyl magnesium bromide (23 mL, 2.0M in diethyl ether, 46 mmol) is slowly added to the reaction over 1 h. The reaction is allowed to warm slowly to room temperature and monitored by TLC. Upon complete consumption of starting material, the reaction is carefully neutralized with 1N hydrochloric acid, extracted with diethyl ether, washed, dried, and concentrated. The 1-(6-chloro-pyridin-3-yl)-hexan-1-one (5.2 g, 24.8 mmol) 80% yield, is used without further purification.

Workup

  1. temperatureto warm slowly to room temperature
  2. customUpon complete consumption of starting material
  3. extractionextracted with diethyl ether
  4. washwashed
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3139c07f281544a9805a57c70a44e10f
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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