1,1'-Carbonyldiimidazole → N-Methoxy-N,2,6-trimethylisonicotinamide

HRID 926493Notes

Reaction equation

HRID 926493 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH3:11])[N:10]=1)[C:5](O)=[O:6].C1N=CN(C(N2C=NC=C2)=O)C=1.Cl.[CH3:25][NH:26][O:27][CH3:28]>C(Cl)Cl>[CH3:28][O:27][N:26]([CH3:25])[C:5](=[O:6])[C:4]1[CH:3]=[C:2]([CH3:1])[N:10]=[C:9]([CH3:11])[CH:8]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 45318962,6-Dimethylpyridine-4-carboxylic acid

Product 1

HCID 18736278N-Methoxy-N,2,6-trimethylisonicotinamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2,6-dimethylisonicotinic acid (1.00 g, 6.61 mmol) in DCM (8.3 mL), CDI (1.18 g, 7.27 mmol) was added and the mixture was stirred for 45 minutes after which N,O-dimethylhydroxylamine hydrochloride (0.71 g, 7.3 mmol) was added and the mixture was stirred for 20 hours. The reaction mixture was quenched with 0.3 M aqueous solution of NaOH and partitioned between water and DCM. The aqueous layer was extracted with DCM, washed with aqueous saturated solution of NaCl, dried (MgSO4) and concentrated. The crude product was purified by flash column chromatography (silica gel, 0-100% EtOAc-DCM) to provide the title compound.

Workup

  1. additionwas added
  2. customThe reaction mixture was quenched with 0.3 M aqueous solution of NaOH
  3. custompartitioned between water and DCM
  4. extractionThe aqueous layer was extracted with DCM
  5. washwashed with aqueous saturated solution of NaCl
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe crude product was purified by flash column chromatography (silica gel, 0-100% EtOAc-DCM)

Sources & evidence

ORD record
ord-e89c6036b7d045508c3805ad149ec7ed
Source dataset
uspto-grants-2016_03
Patent number
US09284308B2

Reaction notes

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