Sodium Chloride → 6-methoxy-1-methyl-3,4-dihydro-1H-[1,5]naphthyridin-2-one

HRID 1244055ノート

反応式

HRID 1244055 の反応式
[CH3:1][O:2][C:3]1[N:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[CH2:7][CH2:6]2.[CH3:14]C(C)([O-])C.[K+].CI.[Na+].[Cl-]>CN(C=O)C>[CH3:1][O:2][C:3]1[N:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH3:14])[C:8](=[O:13])[CH2:7][CH2:6]2

参加物

6

反応物 4

HCID 5234Sodium ChlorideHCID 6328Methyl iodideHCID 219318756-methoxy-3,4-dihydro-1H-[1,5]naphthyridin-2-oneHCID 23665647Potassium tert-butoxide

生成物 1

HCID 219316936-methoxy-1-methyl-3,4-dihydro-1H-[1,5]naphthyridin-2-one収率 64.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of 1.2 g (6.7 mmol) 6-methoxy-3,4-dihydro-1H-[1,5]naphthyridin-2-one in 15 ml of DMF was cooled to 5° C. and to this solution was slowly added 6.7 ml (6.7 mmol) of potassium t-butoxide (1M solution in THF). The mixture was stirred for 10 minutes followed by addition of 0.46 ml (7.4 mmol) methyl iodide. After addition was complete, the reaction mixture was stirred for 1 hour at 5° C. The reaction mixture was poured into saturated NaCl. The mixture was extracted with ethyl acetate. The ethyl acetate extracts were dried (Na2SO4) and evaporated. The residue was chromatographed on silica using 5:1 chloroform/ethyl acetate as the elutant. Appropriate fractions were combined and evaporated to yield 0.83 g of 6-methoxy-1-methyl-3,4-dihydro-1H-[1,5]naphthyridin-2-one. TLC Rf=0.6 (1:10 ethyl acetate/chloroform). 1H NMR (CDCl3) δ 7.2 (d, 1H), 6.6 (d, 1H), 3.9 (s, 3H), 3.3 (s, 3H), 3.0 (m, 2H), 2.7 (m, 2H). Mass Spectrum: m/e 193.2 (p+1).

後処理

  1. additionAfter addition
  2. stirringthe reaction mixture was stirred for 1 hour at 5° C
  3. extractionThe mixture was extracted with ethyl acetate
  4. dry with materialThe ethyl acetate extracts were dried (Na2SO4)
  5. customevaporated
  6. customThe residue was chromatographed on silica using 5:1 chloroform/ethyl acetate as the elutant
  7. customevaporated

出典と根拠

ORDレコード
ord-4f2957189031418a90e3e9f7a5368829
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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