7-nitro-3,4-dihydro-2H-1,4-benzoxazin-3-one → 7-amino-3,4-dihydro-2H-1,4-benzoxazin-3-one

HRID 641943

반응식

HRID 641943 반응식
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[NH:12][C:11](=[O:13])[CH2:10][O:9][C:8]=2[CH:14]=1)([O-])=O.[H][H]>CN(C=O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]2[NH:12][C:11](=[O:13])[CH2:10][O:9][C:8]=2[CH:14]=1

참가 물질

5

반응물 2

HCID 27638307-nitro-3,4-dihydro-2H-1,4-benzoxazin-3-oneHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 27641827-amino-3,4-dihydro-2H-1,4-benzoxazin-3-one

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 6228Dimethylformamide용매

실험 절차

Into 500 mL 3-necked round bottom flask was added a solution of 7-nitro-2H-benzo[b][1,4]oxazin-3(4H)-one (12 g, 61.86 mmol) in DMF (150 mL). To the mixture was added Pd/C (5 g) followed by addition of hydrogen gas. The resulting solution was allowed to react, with stirring, overnight while the temperature was maintained at room temperature. The reaction progress was monitored by TLC (ethyl acetate/petroleum ether=1:1). A filtration was performed. The filtrate was concentrated by evaporation under vacuum using a rotary evaporator. The product was precipitated by the addition of H2O. A filtration was performed. The filter cake was washed 3 times with 300 mL of hexane. This resulted in 7.3 g (68%) of 7-amino-2H-benzo[b][1,4]oxazin-3(4H)-one as a yellow solid.

후처리

  1. customto react
  2. filtrationA filtration
  3. concentrationThe filtrate was concentrated by evaporation under vacuum
  4. customa rotary evaporator
  5. customThe product was precipitated by the addition of H2O
  6. filtrationA filtration
  7. washThe filter cake was washed 3 times with 300 mL of hexane
  8. customThis resulted in 7.3 g (68%) of 7-amino-2H-benzo[b][1,4]oxazin-3(4H)-one as a yellow solid

출처 및 근거

ORD 기록
ord-7a75ea99eb954f7386661d1c4dcd07e8
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696229B2

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