8-Bromo-1,2,3,4-tetrahydro-2-methyl-6-nitro-5-isoquinolinamine → 1,2,3,4-Tetrahydro-2-methyl-5,6-isoquinolinediamine

HRID 48205ノート

反応式

HRID 48205 の反応式
Br[C:2]1[C:11]2[CH2:10][N:9]([CH3:12])[CH2:8][CH2:7][C:6]=2[C:5]([NH2:13])=[C:4]([N+:14]([O-])=O)[CH:3]=1>CO.[Pd]>[CH3:12][N:9]1[CH2:8][CH2:7][C:6]2[C:11](=[CH:2][CH:3]=[C:4]([NH2:14])[C:5]=2[NH2:13])[CH2:10]1

参加物

4

反応物 1

HCID 100168198-Bromo-1,2,3,4-tetrahydro-2-methyl-6-nitro-5-isoquinolinamine

生成物 1

HCID 104197311,2,3,4-Tetrahydro-2-methyl-5,6-isoquinolinediamine収率 48.5%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

A solution of the product from Example 10 (1.50 g, 5.24 mmol) and 20% Pd on carbon (0.30 g) in 100 mL of MeOH was hydrogenated at room temperature and pressure for 24 hours. The reaction mixture was filtered and the filtrate concentrated. The residue was partitioned between CHCl3 and saturated aqueous NaHCO3 solution. The organic phase was separated and the aqueous phase was extracted with additional CHCl3 and the combined organic extracts were dried (Na2SO4), filtered, and concentrated. The residue was filtered through a plug of silica gel eluting with 25% EtOH/EtOAc. The eluant was concentrated to give the title compound as an oil (0.45 g, 48%).

後処理

  1. customwas hydrogenated at room temperature
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate concentrated
  4. customThe residue was partitioned between CHCl3 and saturated aqueous NaHCO3 solution
  5. customThe organic phase was separated
  6. extractionthe aqueous phase was extracted with additional CHCl3
  7. dry with materialthe combined organic extracts were dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. filtrationThe residue was filtered through a plug of silica gel eluting with 25% EtOH/EtOAc
  11. concentrationThe eluant was concentrated

出典と根拠

ORDレコード
ord-b576187f356f4ac0a5116c77df25f56f
出典データセット
uspto-grants-2004_03
特許番号
US06703391B2

反応ノート

読み込み中…