Water → 7-bromo-6-methoxy-1-methyl-3,4-dihydro-1H-[1,5]naphthyridin-2-one

HRID 1244056노트

반응식

HRID 1244056 반응식
[CH3:1][O:2][C:3]1[N:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH3:13])[C:8](=[O:14])[CH2:7][CH2:6]2.O.[Br:16]Br>C(O)(=O)C>[Br:16][C:12]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:14])[N:9]2[CH3:13])=[N:4][C:3]=1[O:2][CH3:1]

참가 물질

5

반응물 3

HCID 962Water2회HCID 24408BromineHCID 219316936-methoxy-1-methyl-3,4-dihydro-1H-[1,5]naphthyridin-2-one

생성물 1

HCID 219318227-bromo-6-methoxy-1-methyl-3,4-dihydro-1H-[1,5]naphthyridin-2-one수율 82.1%

시약·촉매·용매 1

HCID 176Acetic Acid용매

반응 조건

온도
60 °C

실험 절차

To a solution of 0.6 g (3.1 mmol) 6-methoxy-1-methyl-3,4-dihydro-1H-[1,5]naphthyridin-2-one in 8 ml of acetic acid was added 8 ml of water. To this mixture was added 0.32 ml (6.2 mmol) of bromine. The reaction mixture was heated to 60° C. for 1 hour. The reaction mixture was cooled to room temperature and poured into 50 ml of water. The suspension was extracted with ethyl acetate. The ethyl acetate extracts were dried (Na2SO4) and evaporated. The residue was chromatographed on silica using chloroform as the elutant. Appropriate fractions were combined and evaporated to yield 0.69 g of 7-bromo-6-methoxy-1-methyl-3,4-dihydro-1H-[1,5]naphthyridin-2-one. TLC Rf=0.8 (10:1 ethyl acetate/chloroform). 1H NMR (CDCl3) δ 7.42 (s, 1H), 4.0 (s, 3H), 3.3 (s, 3H), 3.0 (m, 2H), 2.7 (m, 2H). Mass Spectrum: m/e=271.2, 273.2 (p+1,3).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionThe suspension was extracted with ethyl acetate
  3. dry with materialThe ethyl acetate extracts were dried (Na2SO4)
  4. customevaporated
  5. customThe residue was chromatographed on silica
  6. customevaporated

출처 및 근거

ORD 기록
ord-cec80924ba564619b05e51df103c37c2
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07119207B2

반응 노트

불러오는 중…