Methanol → 6,7,8,9-tetrahydro-5H-pyrido[3,2-b]azepine

HRID 1733958ノート

反応式

HRID 1733958 の反応式
[N:1]1[C:11]2[CH2:10][CH2:9][CH2:8][C:7](=O)[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].CO>O1CCCC1>[N:1]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

参加物

5

反応物 3

HCID 887MethanolHCID 122830325H,6H,7H,8H,9H-pyrido(3,2-b)azepin-6-oneHCID 21226445Aluminium lithium hydride

生成物 1

HCID 124131726,7,8,9-tetrahydro-5H-pyrido[3,2-b]azepine収率 70.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 1.56 g of 5,7,8,9-tetrahydro-6H-pyrido[3,2-b]azepine-6-one, 3.31 g of lithium aluminum hydride in 40 ml of tetrahydrofuran is refluxed for 4 hours. The mixture is cooled (0° C.) and 25 ml of methanol is added dropwise. The mixture is filtered through diatomaceous earth, the filter cake washed with tetrahydrofuran and the filtrate concentrated to dryness under vacuum. Water (50 ml) is added to the residue and the mixture extracted with diethyl ether. The extract is dried (Na2SO4) and filtered through a thin pad of hydrous magnesium silicate (pad washed with) diethyl ether. The filtrate is concentrated under vacuum to give 1.01 g of crystals, m.p. 70°-71° C.

後処理

  1. temperatureis refluxed for 4 hours
  2. additionis added dropwise
  3. filtrationThe mixture is filtered through diatomaceous earth
  4. washthe filter cake washed with tetrahydrofuran
  5. concentrationthe filtrate concentrated to dryness under vacuum
  6. additionWater (50 ml) is added to the residue
  7. extractionthe mixture extracted with diethyl ether
  8. dry with materialThe extract is dried (Na2SO4)
  9. filtrationfiltered through a thin pad of hydrous magnesium silicate (pad washed with) diethyl ether
  10. concentrationThe filtrate is concentrated under vacuum

出典と根拠

ORDレコード
ord-8df1eec7647348ebac69b88cf384f641
出典データセット
uspto-grants-1996_07
特許番号
US05532235

反応ノート

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