Pyridine → 3-Bromo-6-chloro-N-methoxy-N-methylpicolinamide

HRID 2401409Notes

Reaction equation

HRID 2401409 reaction equation
[Br:1][C:2]1[C:3]([C:9]([OH:11])=O)=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1.Cl.[CH3:13][NH:14][O:15][CH3:16].N1C=CC=CC=1.Cl.C(N=C=NCCCN(C)C)C.[Cl-].[NH4+]>C(Cl)Cl>[Br:1][C:2]1[C:3]([C:9]([N:14]([O:15][CH3:16])[CH3:13])=[O:11])=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 1049PyridineHCID 25517Ammonium ChlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 269667323-Bromo-6-chloropyridine-2-carboxylic acid

Product 1

HCID 866667253-Bromo-6-chloro-N-methoxy-N-methylpicolinamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-bromo-6-chloropicolinic acid (4.516 g, 19.10 mmol), N,O-dimethylhydroxylamine hydrochloride (3.73 g, 38.2 mmol), pyridine (4.63 mL, 57.3 mmol) in CH2Cl2 (40 mL) at 0° C. was added —N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (4.39 g, 22.92 mmol). After 1 h at 0° C., a saturated aqueous solution of ammonium chloride was added and the product was extracted with MTBE/EtOAc (4:1) (repeated 4 times). The organic layers were combined, dried over Na2SO4 and concentrated to dryness. The product was carried out without purification in the next step. LC/MS m/z 281 [M+H]+.

Workup

  1. extractionthe product was extracted with MTBE/EtOAc (4:1) (repeated 4 times)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated to dryness
  4. customThe product was carried out without purification in the next step

Sources & evidence

ORD record
ord-c16c1942239a4e66ae169960c651d2a5
Source dataset
uspto-grants-2014_08
Patent number
US08796261B2

Reaction notes

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