Sodium Methoxide → 7-Chloro-1,5-naphthyridin-2(1H)-one

HRID 2364591

반응식

HRID 2364591 반응식
[NH2:1][C:2]1[C:3](/[CH:9]=[CH:10]/[C:11]([O:13]C)=O)=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.C[O-].[Na+]>C(O)C>[Cl:8][C:6]1[CH:7]=[C:2]2[C:3]([CH:9]=[CH:10][C:11](=[O:13])[NH:1]2)=[N:4][CH:5]=1

참가 물질

4

반응물 2

HCID 10942334Sodium MethoxideHCID 86705409(E)-methyl 3-(3-amino-5-chloropyridin-2-yl)acrylate

생성물 1

HCID 401522397-Chloro-1,5-naphthyridin-2(1H)-one

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A suspension of (E)-methyl 3-(3-amino-5-chloropyridin-2-yl)acrylate (1.2 g, 5.64 mmol) and sodium methoxide (0.786 ml, 14.11 mmol) in 20 mL of ethanol was refluxed for 3 h until the starting material disappeared. The reaction mixture was evaporated to dryness to give crude product 7-chloro-1,5-naphthyridin-2(1H)-one. To the crude residue was added phosphorus oxychloride (5.17 ml, 56.4 mmol) and the resulting mixture was stirred at 70° C. for 4 h. The excess POCl3 was removed under reduced pressure and the residue was directly submitted to flash column (DCM) to give 2,7-dichloro-1,5-naphthyridine (540 mg, 2.71 mmol, 48.1% yield) as an off-white solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm=8.90 (d, J=2.2 Hz, 1H), 8.35 (d, J=8.8 Hz, 1H), 8.31 (d, J=1.8 Hz, 1H), 7.63 (d, J=8.8 Hz, 1H). m/z=199 (M+1).

후처리

  1. temperaturewas refluxed for 3 h until the starting material
  2. customThe reaction mixture was evaporated to dryness

출처 및 근거

ORD 기록
ord-43bc216759a64ee0b2afa7cacfd7ae03
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08691986B2

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