1-(Tetrahydropyran-4-yl)amino-2-nitro-4-trifluoromethylbenzene → 2-Amino-1-(tetrahydropyran-4-yl)amino-4-trifluoromethylbenzene

HRID 74151

반응식

HRID 74151 반응식
[O:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][C:9]=2[N+:18]([O-])=O)[CH2:3][CH2:2]1.[H][H]>[C].[Pd].O1CCCC1>[NH2:18][C:9]1[CH:10]=[C:11]([C:14]([F:16])([F:17])[F:15])[CH:12]=[CH:13][C:8]=1[NH:7][CH:4]1[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1

참가 물질

5

반응물 2

HCID 185098281-(Tetrahydropyran-4-yl)amino-2-nitro-4-trifluoromethylbenzeneHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 185097862-Amino-1-(tetrahydropyran-4-yl)amino-4-trifluoromethylbenzene수율 73.6%

시약·촉매·용매 2

HCID 178418390HCID 178418390, 화합물촉매HCID 8028Tetrahydrofuran용매

실험 절차

A 3-neck flask (200 mL) was charged with 1-(tetrahydropyran-4-yl)amino-2-nitro-4-trifluoromethylbenzene (see Synthesis Example 4-1) (1.00 g, 3.45 mmol) and tetrahydrofuran (17 mL), and this was shaken to give a homogeneous solution. To this was added palladium-carbon (Pd: 10%, 0.09 g), and this was again shaken. Hydrogen was substituted in by successively reducing the pressure and purging with hydrogen gas 3 times, and after vigorous shaking at room temperature under these conditions for 4 h, this was purged with nitrogen, distilled water (40 mL) was added and this was shaken for 10 minutes, then insoluble material was filtered off through a Celite layer (20 mm thickness), and this same layer was further washed with ethyl acetate. The filtrate and wash solutions were combined and the solvent was distilled off under reduced pressure to yield the title compound (0.66 g, 73.6% yield) as a white powder.

후처리

  1. customto give a homogeneous solution
  2. stirringthis was again shaken
  3. custompurging with hydrogen gas 3 times
  4. stirringafter vigorous shaking at room temperature under these conditions for 4 h
  5. customthis was purged with nitrogen
  6. distillationdistilled water (40 mL)
  7. additionwas added
  8. stirringthis was shaken for 10 minutes
  9. filtrationinsoluble material was filtered off through a Celite layer (20 mm thickness)
  10. washthis same layer was further washed with ethyl acetate
  11. washThe filtrate and wash solutions
  12. distillationthe solvent was distilled off under reduced pressure

출처 및 근거

ORD 기록
ord-df086b7629b846fea1628b3266de05d8
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829035B2

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