Picolinic acid → N-(3-methoxyphenyl)picolinamide

HRID 38239노트

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HRID 38239 반응식
[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

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
50 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2e32cc9db14340eebcd922f15264f743
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524726B2

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