Hydrazine → 6-Amino-2,3-dihydro-4H-1-benzopyran-4-one

HRID 493140노트

반응식

HRID 493140 반응식
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[O:10][CH2:9][CH2:8][C:7]2=[O:14])([O-])=O.NN>[Ni].C(O)C>[NH2:1][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[O:10][CH2:9][CH2:8][C:7]2=[O:14]

참가 물질

5

반응물 2

HCID 9321HydrazineHCID 52288316-nitro-3,4-dihydro-2H-1-benzopyran-4-one

생성물 1

HCID 200709836-Amino-2,3-dihydro-4H-1-benzopyran-4-one수율 75%

시약·촉매·용매 2

HCID 935Nickel촉매HCID 702Ethanol용매

실험 절차

Under an inert atmosphere, a mixture of 6-nitro-2,3-dihydro-4H-chromen-4-one (5.4 g, 28 mmol), ethanol (250 mL), Raney nickel (1.5 g) and anhydrous hydrazine (8.8 mL, 0.28 mol) is stirred at ambient temperature overnight and filtered. The clear filtrate is concentrated to near dryness in vacuo. The resultant residue is treated with 6N hydrochloric acid and heated at reflux temperature for 1 hour, cooled in an ice bath, rendered basic with sodium bicarbonate and extracted with ethyl acetate. The organic phase is washed with brine, dried over MgSO4 and concentrated in vacuo to afford the title compound as a yellow crystalline solid, 3.4 g (75% yield), mp 136-137° C., identified by NMR and mass spectral analyses.

후처리

  1. filtrationfiltered
  2. concentrationThe clear filtrate is concentrated
  3. additionThe resultant residue is treated with 6N hydrochloric acid
  4. temperatureheated
  5. temperatureat reflux temperature for 1 hour
  6. temperaturecooled in an ice bath
  7. extractionextracted with ethyl acetate
  8. washThe organic phase is washed with brine
  9. dry with materialdried over MgSO4
  10. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-b28dbff6a50b4475852c8dfae9521bdd
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07534801B2

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