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

HRID 493140

反応式

HRID 493140 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 935Nickel触媒HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b28dbff6a50b4475852c8dfae9521bdd
出典データセット
uspto-grants-2009_05
特許番号
US07534801B2

関連ノート

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