6-Fluoro-2H-1,4-benzoxazin-3(4H)-one → 6-Fluoro-3,4-dihydro-2H-1,4-benzoxazine

HRID 1515339노트

반응식

HRID 1515339 반응식
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][C:8](=O)[NH:7][C:6]=2[CH:12]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1.N>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][CH2:8][NH:7][C:6]=2[CH:12]=1

참가 물질

5

반응물 2

HCID 3028976-Fluoro-2H-1,4-benzoxazin-3(4H)-oneHCID 21226445Aluminium lithium hydride

생성물 1

HCID 162444596-Fluoro-3,4-dihydro-2H-1,4-benzoxazine수율 98.2%

시약·촉매·용매 2

HCID 222Ammonia용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 6-fluoro-2H-1,4-benzoxazin-3(4H)-one (1.5 g) in tetrahydrofuran (30 ml), lithium aluminum hydride (683 mg) was added under ice cooling and heated under reflux for 3.5 hours. The reaction mixture was cooled to room temperature, diluted with 28% aqueous ammonia under ice cooling, and then filtered to remove insoluble materials. The filtrate was evaporated under reduced pressure to remove the solvent. The resulting residue was purified by silica gel column chromatography (eluting solvent: n-hexane:ethyl acetate=20:1 to 5:1) to give the titled compound, i.e., 6-fluoro-3,4-dihydro-2H-1,4-benzoxazine (1.35 g) as a red oil.

후처리

  1. temperatureheated
  2. temperatureunder reflux for 3.5 hours
  3. filtrationfiltered
  4. customto remove insoluble materials
  5. customThe filtrate was evaporated under reduced pressure
  6. customto remove the solvent
  7. customThe resulting residue was purified by silica gel column chromatography (eluting solvent: n-hexane:ethyl acetate=20:1 to 5:1)

출처 및 근거

ORD 기록
ord-8eaec25189304ad7b89a3292151fd42b
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08222417B2

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