1,2-Dichloroethane → 2-Bromo-N-methoxy-N-methylisonicotinamide

HRID 1909015Notes

Reaction equation

HRID 1909015 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5](O)=[O:6].C1C=CC2N(O)N=NC=2C=1.Cl.[CH3:22][O:23][NH:24][CH3:25].C(Cl)CCl>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([N:24]([O:23][CH3:22])[CH3:25])=[O:6]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 2227012-Bromoisonicotinic acid

Product 1

HCID 448186542-Bromo-N-methoxy-N-methylisonicotinamideYield 75.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 2-bromoisonicotinic acid, (25.2 g, 124 mmol), HOBt (20.2 g, 149 mmol) and O,N-dimethyl-hydroxylamine hydrochloride (14.6 g, 149 mmol) in DMF (150 mL) at 0° C., was added diisopropylethyalamine (26.0 mL, 149 mmol). EDC (28.6 g, 149 mmol) was then added and the mixture stirred at room temperature for 1 hour. The mixture was then poured into ice cold water (500 mL) and the resulting solution extracted with EtOAc (3×150 mL). The combined organic fraction was were washed with water (2×200 mL), 0.5 M HCl (200 mL), sat. NaHCO3 solution, brine (200 mL) and then dried (MgSO4). The solvent was evaporated in vacuo to give 2-bromo-N-methoxy-N-methyl-isonicotinamide (23 g, 75%)

Workup

  1. extractionthe resulting solution extracted with EtOAc (3×150 mL)
  2. washThe combined organic fraction was were washed with water (2×200 mL), 0.5 M HCl (200 mL), sat. NaHCO3 solution, brine (200 mL)
  3. dry with materialdried (MgSO4)
  4. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-efa39d306387460380a61bf698682009
Source dataset
uspto-grants-2013_12
Patent number
US08598217B2

Reaction notes

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