Aluminium lithium hydride → 7-methyl-3-phenyl-2,3-dihydro-4H-1,4-benzoxazin-4-amine

HRID 585445ノート

反応式

HRID 585445 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[CH:25]=[CH:24][C:11]2[N:12]([N:22]=O)[CH:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:14][O:15][C:10]=2[CH:9]=1>C(OCC)C.C1COCC1.CCCCCC>[CH3:7][C:8]1[CH:25]=[CH:24][C:11]2[N:12]([NH2:22])[CH:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:14][O:15][C:10]=2[CH:9]=1

参加物

6

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 223363397-methyl4-nitroso-3-phenyl-3,4-dihydro-2H-1,4-benzoxazine

生成物 1

HCID 223363427-methyl-3-phenyl-2,3-dihydro-4H-1,4-benzoxazin-4-amine収率 75.2%

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒2 回HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

実験手順

A slurry of lithium aluminum hydride (6.9 g, 183 mmol) in ethyl ether (300 mL) is stirred in an ice bath under an argon atmosphere. A solution of 7-methyl-4-nitroso-3-phenyl-3,4-dihydro-2H-1,4-benzoxazine (23.22 g, 91.3 mmol) in ethyl ether (250 mL) and dry THF (40 mL) is added dropwise over 1.5 h. The mixture is removed from the ice bath and allowed to stir for 18 h. Water (50 mL) is slowly added, forming solids. The solids are collected by filtration and washed with ethyl ether. The resulting filtrates are combined and washed three times with water (400 mL), dried over magnesium sulfate, and concentrated to dryness to give a solid. The solids are slurried in hexane, collected, and dried to give 16.5 g (69%) of 7-methyl-3-phenyl-2,3-dihydro-4H-1,4-benzoxazin-4-amine.

後処理

  1. customThe mixture is removed from the ice bath
  2. additionWater (50 mL) is slowly added
  3. customforming solids
  4. filtrationThe solids are collected by filtration
  5. washwashed with ethyl ether
  6. washwashed three times with water (400 mL)
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated to dryness
  9. customto give a solid
  10. customcollected
  11. customdried

出典と根拠

ORDレコード
ord-09b48926929c41158c5ca72293c114c0
出典データセット
uspto-grants-2005_08
特許番号
US06932961B1

反応ノート

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