Ammonium Acetate → 4-((3,5-dichloropyridin-2-yl)methoxy)pyridin-2(1H)-one

HRID 474946노트

반응식

HRID 474946 반응식
[Cl:1][C:2]1[C:3]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][N:14]=[C:13](Cl)[CH:12]=2)=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.C([O-])(=[O:20])C.[NH4+]>C(O)=O.O>[Cl:1][C:2]1[C:3]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][NH:14][C:13](=[O:20])[CH:12]=2)=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1

참가 물질

5

반응물 2

HCID 517165Ammonium AcetateHCID 580934283,5-Dichloro-2-((2-chloropyridin-4-yloxy)methyl)pyridine

생성물 1

HCID 580933734-((3,5-dichloropyridin-2-yl)methoxy)pyridin-2(1H)-one수율 83.3%

시약·촉매·용매 2

HCID 284Formic Acid용매HCID 962Water용매

실험 절차

3,5-Dichloro-2-((2-chloropyridin-4-yloxy)methyl)pyridine (1.15 g, 4.03 mmol) and ammonium acetate (1.55 g, 20.0 mmol) were heated to 110° C. in a mixture of formic acid (20 mL) and water (20 mL) for 5 days. The mixture was concentrated to remove most of the liquid and then adjusted to pH 8 with NaHCO3 solution. The solid was filtered off to provide the title compound (910 mg, 82%) as a tan solid: 1H NMR (300 MHz, DMSO-d6) δ 11.1 (br s, 1H), 8.66 (d, J=2.1 Hz, 1H), 8.34 (d, J=2.1 Hz, 1H), 7.25 (d, J=7.3 Hz, 1H), 5.90-5.87 (dd, J=7.3, 2.8 Hz, 1H), 5.82 (d, J=2.6 Hz, 1H), 5.20 (s, 2H).

후처리

  1. concentrationThe mixture was concentrated
  2. customto remove most of the liquid
  3. filtrationThe solid was filtered off

출처 및 근거

ORD 기록
ord-c027047ff47c4f8d9eea16e9665f1500
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637501B2

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