Methanol → HCID 10607526、化合物

HRID 1420675ノート

反応式

HRID 1420675 の反応式
[C:1]1(=O)[C:12]2=[C:13]3[C:8](=[CH:9][CH:10]=[CH:11]2)[CH:7]=[CH:6][CH:5]=[C:4]3[CH2:3][CH2:2]1.Cl.[NH2:16]O.CO.C([O-])(=O)C.[Na+]>O>[CH:1]1([NH2:16])[C:12]2=[C:13]3[C:8](=[CH:9][CH:10]=[CH:11]2)[CH:7]=[CH:6][CH:5]=[C:4]3[CH2:3][CH2:2]1

参加物

6

反応物 4

HCID 887MethanolHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 6027812,3-Dihydro-1H-phenalen-1-one

生成物 1

HCID 10607526HCID 10607526、化合物収率 71.6%

試薬・触媒・溶媒 1

HCID 962Water溶媒3 回

実験手順

To a stirred mixture of 2,3-dihydro-phenalen-1-one (1.32 g, 7.24 mmol), hydroxylamine hydrochloride (0.85 g, 12.2 mmol) and water (6 ml) was added dropwise at 75° C. MeOH (7.5 ml) and afterwards a solution of sodium acetate (2.58 g, 19.0 mmol) in water (4 ml). Stirring was continued over a period of 1.5, h, water (20 ml) was added and after cooling (ice bath) the solid was collected by filtration. After drying in vacuo the crude product was dissolved in 3.5 N NH3 /MeOH (100 ml) and hydrogenated over Raney-Nickel (0.5 g, washed with MeOH) at RT for 17h. The catalyst was filtered off, the solution evaporated in vacuo and the residue purified by column chromatography on silica gel (dichloromethane/MeOH 9:1) to yield (RS)-2,3-dihydro-1H-phenalen-1-yl-amine (0.95 g) as a brown oil.

後処理

  1. additionwas added dropwise at 75° C
  2. additionwas added
  3. temperatureafter cooling (ice bath) the solid
  4. filtrationwas collected by filtration
  5. dry with materialAfter drying in vacuo the crude product
  6. dissolutionwas dissolved in 3.5 N NH3 /MeOH (100 ml) and hydrogenated over Raney-Nickel (0.5 g, washed with MeOH) at RT for 17h
  7. filtrationThe catalyst was filtered off
  8. customthe solution evaporated in vacuo
  9. customthe residue purified by column chromatography on silica gel (dichloromethane/MeOH 9:1)

出典と根拠

ORDレコード
ord-e061e39338044ee19378bc581f681886
出典データセット
uspto-grants-2000_06
特許番号
US06071925

反応ノート

読み込み中…