Picolinic acid → N-(3-methoxyphenyl)picolinamide

HRID 38239Notes

Reaction equation

HRID 38239 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6].[N:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16](O)=[O:17].CCN=C=NCCCN(C)C.Cl.CCN(CC)CC.OC1C2N=NNC=2C=CC=1>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:6][C:16](=[O:17])[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][N:10]=2)[CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 5

HCID 1018Picolinic acidHCID 8471TriethylamineHCID 108243-MethoxyanilineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178418300HCID 178418300, compound

Product 1

HCID 22565221N-(3-methoxyphenyl)picolinamideYield 90.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

According to Scheme 1 Method B: 3-Methoxyaniline (1.62 mmol, 0.18 mL) was added to a solution of picolinic acid (1.62 mmol, 0.20 g), EDCI.HCl (2.44 mmol, 0.47 g), Et3N (3.25 mmol, 0.45 mL), hydroxybenzotriazole (1.95 mmol, 0.30 g) in DCM (6 mL) at room temperature. The reaction mixture was stirred at 50° C. for 12 hours. The organic phase was washed with a saturated solution of NaHCO3 and with brine, was dried over MgSO4, was filtered and was concentrated under reduced pressure. The crude product was purified by flash chromatography over silica gel using cyclohexane/AcOEt (90:10) as eluent to afford N-(3-methoxyphenyl)picolinamide (1.46 mmol, 0.33 g, 90%) as an orange liquid.

Workup

  1. washThe organic phase was washed with a saturated solution of NaHCO3 and with brine
  2. dry with materialwas dried over MgSO4
  3. filtrationwas filtered
  4. concentrationwas concentrated under reduced pressure
  5. customThe crude product was purified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-2e32cc9db14340eebcd922f15264f743
Source dataset
uspto-grants-2013_09
Patent number
US08524726B2

Reaction notes

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