4-Hydroxybenzaldehyde → 6-(4-Formylphenoxy)pyridine-3-carboxamide

HRID 130739

반응식

HRID 130739 반응식
Cl[C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][N:3]=1.[OH:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH:16]([C:15]1[CH:18]=[CH:19][C:12]([O:11][C:2]2[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][N:3]=2)=[CH:13][CH:14]=1)=[O:17]

참가 물질

6

반응물 4

HCID 1264-HydroxybenzaldehydeHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 804566-Chloronicotinamide

생성물 1

HCID 568514226-(4-Formylphenoxy)pyridine-3-carboxamide수율 46%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
130 °C

실험 절차

Combine 6-chloronicotinamide (4.53 g, 28.9 mmol), 4-hydroxybenzaldehyde (3.5 g, 28.9 mmol), potassium carbonate (6 g, 43.4 mmol), and dimethylformamide (200 mL). Heat the reaction mixture to 130° C. under nitrogen, and stir for 18 h. Dilute the reaction mixture with 200 mL of water, extract with diethyl ether (4×100 mL) and dichloroethane (2×100 mL). Combine the organics, and dry over magnesium sulfate. Filter, and concentrate in vacuo. Adsorb the residue on silica, and purify by Biotage Flash 40L (elute with 50:50 hexanes/ethyl acetate to 100% ethyl acetate) to afford the title compound as a white solid (3.2 g, 46%): 1H NMR (DMSO-d6): 10.0 (s, 1H), 8.59 (d, 1H), 8.26-8.22 (dd, 1H), 7.98-7.95 (m, 2H), 7.10-7.07 (d, 1H), 6.15-5.65 (br m, 2H).

후처리

  1. extractionextract with diethyl ether (4×100 mL) and dichloroethane (2×100 mL)
  2. dry with materialCombine the organics, and dry over magnesium sulfate
  3. filtrationFilter
  4. concentrationconcentrate in vacuo
  5. custompurify by Biotage Flash 40L (elute with 50:50 hexanes/ethyl acetate to 100% ethyl acetate)

출처 및 근거

ORD 기록
ord-09322f8fa13b48e8a7a0db8f9c6b500e
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07381719B2

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