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

HRID 1279706노트

반응식

HRID 1279706 반응식
[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

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 3283Diethyl Ether용매2회HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

실험 절차

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-methyl4-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.

후처리

  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

출처 및 근거

ORD 기록
ord-97a07b2b69a7413f863f08051db66a7f
출처 데이터셋
uspto-grants-2002_09
특허 번호
US06448397B1

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