6-nitro-3-(N-propionyl-N-n-propylamino)chroman → 6-amino-3-(N-propionyl-N-n-propylamino)chroman

HRID 1975764노트

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HRID 1975764 반응식
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[O:10][CH2:9][CH:8]([N:14]([C:18](=[O:21])[CH2:19][CH3:20])[CH2:15][CH2:16][CH3:17])[CH2:7]2)([O-])=O>C(O)(=O)C.[Zn]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[O:10][CH2:9][CH:8]([N:14]([C:18](=[O:21])[CH2:19][CH3:20])[CH2:15][CH2:16][CH3:17])[CH2:7]2

참가 물질

4

반응물 1

HCID 108511876-nitro-3-(N-propionyl-N-n-propylamino)chroman

생성물 1

HCID 105634506-amino-3-(N-propionyl-N-n-propylamino)chroman수율 56%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 176Acetic Acid용매

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온도
50 °C

실험 절차

A solution of 6-nitro-3-(N-propionyl-N-n-propylamino)chroman (17) (700 mg, 2.40 mmol) in glacial acetic acid (50 ml) was treated with zinc dust (1.0 g). The mixture was stirred at 50° C. for 90 minutes. The solution was filtered and acetic acid evaporated at reduced pressure. The product was dissolved in CH2Cl2 and washed with 5%-aqueous Na2CO3. The organic layer was separated, dried (Na2SO4) and the solvent was evaporated. The crude product was chromatographed on silica (60 g), with CH2Cl2CH3OH (19:1) as eluant, yielding 350 mg (56%) of 6-amino-3-(N-propionyl-N-n-propylamino)chroman (18) as an oil.

후처리

  1. filtrationThe solution was filtered
  2. customacetic acid evaporated at reduced pressure
  3. dissolutionThe product was dissolved in CH2Cl2
  4. washwashed with 5%-aqueous Na2CO3
  5. customThe organic layer was separated
  6. dry with materialdried (Na2SO4)
  7. customthe solvent was evaporated
  8. customThe crude product was chromatographed on silica (60 g), with CH2Cl2CH3OH (19:1) as eluant

출처 및 근거

ORD 기록
ord-3abe83edc7584468a3b2a394556ddf15
출처 데이터셋
uspto-grants-1994_02
특허 번호
US05288748

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