Diethyl Ether → 6-Methoxy-1,5-naphthyridin-4-ol

HRID 1271677ノート

反応式

HRID 1271677 の反応式
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[C:10](OC)(=[O:13])[C:11]#[CH:12].CCOCC>CO.C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>[CH3:9][O:8][C:5]1[N:6]=[C:7]2[C:2](=[CH:3][CH:4]=1)[NH:1][CH:12]=[CH:11][C:10]2=[O:13]

参加物

6

反応物 3

HCID 3283Diethyl EtherHCID 13536Methyl propiolateHCID 811216-Methoxy-3-pyridinylamine

生成物 1

HCID 113788076-Methoxy-1,5-naphthyridin-4-ol収率 70%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)溶媒2 回

実験手順

5-Amino-2-methoxypyridine (55 g, 0.44 mol) in methanol (1000 ml) with methyl propiolate (40 ml, 0.44 mol) was stirred for 48 hours, then evaporated and the product purified by chromatography on silica gel (dichloromethane) followed by recrystallisation from dichloromethane-hexane (44.6 g, 48%). The unsaturated ester (10.5 g, 0.05 mol) in warm Dowtherm A (50 ml) was added over 3 minutes to refluxing Dowtherm A, and after a further 20 minutes at reflux the mixture was cooled and poured into ether. The precipate was filtered to give a white solid (6.26 g, 70%).

後処理

  1. customevaporated
  2. customthe product purified by chromatography on silica gel (dichloromethane)
  3. customfollowed by recrystallisation from dichloromethane-hexane (44.6 g, 48%)
  4. temperatureafter a further 20 minutes at reflux the mixture
  5. temperaturewas cooled
  6. filtrationThe precipate was filtered

出典と根拠

ORDレコード
ord-3a8cfa113d31424082fba6eedaa5d3e3
出典データセット
uspto-grants-2007_04
特許番号
US07205408B2

反応ノート

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