Water → 8-Isopropoxy-1,3,4,5-tetrahydro-2H-benzo[B]azepin-2-one

HRID 518883ノート

反応式

HRID 518883 の反応式
[N-:1]=[N+]=[N-].[Na+].[CH3:5][CH:6]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH2:13][CH2:14][CH2:15][C:16]2=[O:19])=[CH:11][CH:10]=1)[CH3:7].O.C(=O)([O-])[O-].[Na+].[Na+]>FC(F)(F)C(O)=O>[CH3:5][CH:6]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[CH2:13][CH2:14][CH2:15][C:16](=[O:19])[NH:1][C:17]=2[CH:18]=1)[CH3:7]

参加物

6

反応物 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 33557Sodium AzideHCID 142567607-Isopropoxy-3,4-dihydronaphthalen-1(2H)-one

生成物 1

HCID 866980308-Isopropoxy-1,3,4,5-tetrahydro-2H-benzo[B]azepin-2-one収率 14.4%

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

実験手順

900 mg of sodium azide are added at ambient temperature to a solution of 2.24 g of 7-(propan-2-yloxy)-3,4-dihydronaphthalen-1(2H)-one in 35 ml of trifluoroacetic acid. The reaction medium is refluxed for 3 hours and is then brought back to ambient temperature. The reaction medium is poured into 100 ml of water and the pH is adjusted to pH 7 by adding sodium carbonate. The mixture is extracted twice with 100 ml of ethyl acetate. The combined organic phases are dried over magnesium sulfate, filtered and evaporated. The residue is purified by flash chromatography on silica gel, elution being carried out with dichloromethane and then a dichloromethane/methanol (9/1) mixture, so as to obtain 346 mg of 8-(propan-2-yloxy)-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one in the form of an orangey-coloured oil.

後処理

  1. temperatureThe reaction medium is refluxed for 3 hours
  2. customis then brought back to ambient temperature
  3. extractionThe mixture is extracted twice with 100 ml of ethyl acetate
  4. dry with materialThe combined organic phases are dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is purified by flash chromatography on silica gel, elution

出典と根拠

ORDレコード
ord-8e8461cd1d6e488185faff2c5c20f301
出典データセット
uspto-grants-2015_08
特許番号
US09115140B2

反応ノート

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