Nicotinic Acid → N-Methoxy-N-methylnicotinamide

HRID 1157676Notes

Reaction equation

HRID 1157676 reaction equation
C(N(CC)CC)C.[C:8]([OH:16])(=O)[C:9]1[CH:14]=[CH:13][CH:12]=[N:11][CH:10]=1.Cl.[CH3:18][NH:19][O:20][CH3:21].ON1C2C=CC=CC=2N=N1.Cl.CNC(N=C=NCC)CCNC>C(#N)C>[CH3:21][O:20][N:19]([CH3:18])[C:8](=[O:16])[C:9]1[CH:14]=[CH:13][CH:12]=[N:11][CH:10]=1

Participants

7

Reactant 5

HCID 938Nicotinic AcidHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 230638721,3-Dimethylaminopropyl-3-ethylcarbodiimide hydrochloride

Product 1

HCID 10558996N-Methoxy-N-methylnicotinamideYield 98%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Add triethylamine (11.9 mL, 84.5 mmol) dropwise to a suspension of nicotinic acid (10 g, 81.2 mmol), N,O-dimethylhydroxylamine hydrochloride (8.3 g, 85.3 mmol, 1.05 eq), 1-hydroxybenzotriazole (3.29 g, 24.36 mmol, 0.3 eq) and 1,3-dimethylamino propyl-3-ethylcarbodiimide hydrochloride (18.68 g, 97.44 mmol, 1.2 eq) in acetonitrile (100 mL) at room temperature under nitrogen. After 2 h a white precipitate forms. Add water (100 mL) and acetonitrile and evaporate under vacuum. Extract with ethyl acetate (3×100 mL), dry the organic phase over anhydrous sodium sulfate and concentrate to afford 13.19 g (98%) of the title compound.

Workup

  1. customAdd water (100 mL) and acetonitrile and evaporate under vacuum
  2. extractionExtract with ethyl acetate (3×100 mL)
  3. dry with materialdry the organic phase over anhydrous sodium sulfate
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-92a07c202fd342909c5570019760464a
Source dataset
uspto-grants-2010_10
Patent number
US07807691B2

Reaction notes

Loading…