Methanamine, N-methoxy-, hydrochloride (1:1) → 2-Chloro-N-methoxy-N-methylnicotinamide

HRID 717860Notes

Reaction equation

HRID 717860 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].Cl.[CH3:12][NH:13][O:14][CH3:15]>O1CCCC1.C(=O)(O)[O-]>[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([N:13]([O:14][CH3:15])[CH3:12])=[O:5]

Participants

5

Reactant 2

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27745412-Chloronicotinoyl chloride

Product 1

HCID 102360762-Chloro-N-methoxy-N-methylnicotinamideYield 84.7%

Reagents, catalysts & solvents 2

HCID 769Bicarbonate IonSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

2-Chloronicotinoyl chloride (36 g, 0.20 mol) was dissolved in tetrahydrofuran (290 mL) and separately N,O-dimethylhydroxylamine hydrochloride (48 g, 0.49 mol) was stirred in 290 mL saturated bicarbonate solution until the degassing subsided. Then the bicarbonate solution was added to the acid chloride solution and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was extracted with ethyl acetate (2×), dried over sodium sulfate, filtered and evaporated to give the desired product (34 g, 83%). LCMS for C8H10ClN2O2 (M+H)+: m/z=201.0. Found: 200.9.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate (2×)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-a5fdd35ab1e64df7b93de8f22fbf382e
Source dataset
uspto-grants-2015_11
Patent number
US09193721B2

Reaction notes

Loading…