Sodium Carbonate → 6-chloro-N-(cyclopropylmethyl)pyridine-3-carboxamide

HRID 889321Notes

Reaction equation

HRID 889321 reaction equation
Br[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.[CH:11]1([CH2:14][NH2:15])[CH2:13][CH2:12]1.C(=O)([O-])[O-].[Na+].[Na+].S(Cl)([Cl:24])=O>>[Cl:24][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:15][CH2:14][CH:11]2[CH2:13][CH2:12]2)=[O:8])=[CH:4][N:3]=1

Participants

5

Reactant 4

HCID 10340Sodium CarbonateHCID 24386Thionyl ChlorideHCID 75646CyclopropanemethanamineHCID 2389326-Bromonicotinic acid

Product 1

HCID 112758456-chloro-N-(cyclopropylmethyl)pyridine-3-carboxamide

Procedure

6-Bromonicotinic acid (200 mg, 0.99 mmol) was heated at reflux in thionyl chloride (2 ml) for 2.5 hrs. The reaction was allowed to cool to room temperature and the excess thionyl chloride evaporated under vacuum. The residue was dissolved in acetone (4 ml), cyclopropylmethylamine (71 mg, 0.10 mmol) and sodium carbonate (500 mg) were added to the solution. The reaction was stirred at room temperature for 4 hrs, filtered and the filtrate reduced to dryness under vacuum to give 6-chloro-N-cyclopropylmethylnicotinamide as a cream solid. NMR: δH [2H6]-DMSO 8.82,(2H, m), 8.23,(1H, dd), 7.63,(1H, d), 3.14,(2H, t), 1.01,(1H, m), 0.44,(2H, m), 0.22,(2H, m).

Workup

  1. customthe excess thionyl chloride evaporated under vacuum
  2. dissolutionThe residue was dissolved in acetone (4 ml)
  3. filtrationfiltered

Sources & evidence

ORD record
ord-aeb15dbbcbfe4a558d56bba2cb199432
Source dataset
uspto-grants-2012_08
Patent number
US08252818B2

Reaction notes

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