Methanol → 2-Methoxy-5-methyl-6-oxo-5,6,7,8-tetrahydro-[1,5]naphthyridine-3-carbaldehyde

HRID 1244058노트

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HRID 1244058 반응식
[CH3:1][O:2][C:3]1[N:4]=[C:5]2[C:10](=[CH:11][C:12]=1[CH:13]=C)[N:9]([CH3:15])[C:8](=[O:16])[CH2:7][CH2:6]2.C[OH:18]>C(Cl)Cl>[CH3:1][O:2][C:3]1[C:12]([CH:13]=[O:18])=[CH:11][C:10]2[N:9]([CH3:15])[C:8](=[O:16])[CH2:7][CH2:6][C:5]=2[N:4]=1

참가 물질

4

반응물 2

HCID 887MethanolHCID 219317566-methoxy-1-methyl-7-vinyl-3,4-dihydro-1H-[1,5]naphthyridin-2-one

생성물 1

HCID 219317642-Methoxy-5-methyl-6-oxo-5,6,7,8-tetrahydro-[1,5]naphthyridine-3-carbaldehyde

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
-70 °C

실험 절차

A 1.1 g (5.0 mmol) solution of 6-methoxy-1-methyl-7-vinyl-3,4-dihydro-1H-[1,5]naphthyridin-2-one in 50 ml of methylene chloride and 10 ml of methanol was cooled to −70° C. Ozone (via an ozone generator) was bubbled into the solution until a blue color was achieved. The reaction mixture was stirred at −70° C. for 30 minutes and quenched with 4.0 ml of dimethyl sulfide. The reaction mixture was stirred for 18 hours at room temperature. The reaction mixture was poured into 50 ml of water. The organic layer was dried (Na2SO4) and evaporated. This residue was chromatographed on silica using 10:1 chloroform/ethyl acetate as the elutant. Appropriate fractions were combined to yield 0.52 g of 2-methoxy-5-methyl-6-oxo-5,6,7,8-tetrahydro-[1,5]naphthyridine-3-carbaldehyde. TLC Rf=0.4 (1:1 ethyl acetate:hexane). 1H NMR (CDCl3) δ 10.18 (s, 1H), 7.7 (s, 1H), 4.05 (s, 3H), 3.3 (s, 3H), 3.0 (m, 2H), 2.7 (m, 2H). Mass spectrum: m/e=221.1, (p+1).

후처리

  1. customOzone (via an ozone generator) was bubbled into the solution until a blue color
  2. customquenched with 4.0 ml of dimethyl sulfide
  3. stirringThe reaction mixture was stirred for 18 hours at room temperature
  4. additionThe reaction mixture was poured into 50 ml of water
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. customevaporated
  7. customThis residue was chromatographed on silica using 10:1 chloroform/ethyl acetate as the elutant

출처 및 근거

ORD 기록
ord-69dd668f26ed401483ca072142660720
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07119207B2

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