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

HRID 1244056ノート

反応式

HRID 1244056 の反応式
[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]

参加物

5

反応物 3

HCID 962Water2 回HCID 24408BromineHCID 219316936-methoxy-1-methyl-3,4-dihydro-1H-[1,5]naphthyridin-2-one

生成物 1

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
60 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-cec80924ba564619b05e51df103c37c2
出典データセット
uspto-grants-2006_10
特許番号
US07119207B2

反応ノート

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