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

HRID 1975763노트

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HRID 1975763 반응식
[C:1]([N:5]([CH:9]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[O:11][CH2:10]1)[CH2:6][CH2:7][CH3:8])(=[O:4])[CH2:2][CH3:3].[N+:19]([O-])([OH:21])=[O:20].S(=O)(=O)(O)O>[N+](C)([O-])=O>[N+:19]([C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[O:11][CH2:10][CH:9]([N:5]([C:1](=[O:4])[CH2:2][CH3:3])[CH2:6][CH2:7][CH3:8])[CH2:18]2)([O-:21])=[O:20]

참가 물질

5

반응물 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 108481013-(N-propionyl-N-n-propylamino)chroman

생성물 1

HCID 108511876-nitro-3-(N-propionyl-N-n-propylamino)chroman수율 81%

시약·촉매·용매 1

HCID 6375Nitromethane용매

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온도
0 °C

실험 절차

To an ice cool solution of 730 mg (2.96 mmol) 3-(N-propionyl-N-n-propylamino)chroman (16) in nitromethane (15 ml) was a mixture of fuming nitric acid (0.70 ml) and concentrated sulphuric acid (1.42 ml) added. The solution was stirred for 90 min at 0° C. The reaction mixture was poured out on ice and the product was extracted with dichloromethane. The organic layer was washed with water and 5% aqueous Na2CO3. The organic layer was separated, dried (MGSO4) and the solvent was evaporated yielding 700 mg (81%) of 6-nitro-3-(N-propionyl-N-n-propylamino)chroman (17).

후처리

  1. additionadded
  2. additionThe reaction mixture was poured out on ice
  3. extractionthe product was extracted with dichloromethane
  4. washThe organic layer was washed with water and 5% aqueous Na2CO3
  5. customThe organic layer was separated
  6. customdried (MGSO4)
  7. customthe solvent was evaporated

출처 및 근거

ORD 기록
ord-b79d6d13692f4577ad8c5cdfde39a89c
출처 데이터셋
uspto-grants-1994_02
특허 번호
US05288748

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