Nitric Acid → 8-methoxy-5-nitro-3,4-dihydro-1(2H)-naphthalenone

HRID 1633722

반응식

HRID 1633722 반응식
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[C:11](=[O:13])[CH2:10][CH2:9][CH2:8]2.[N+:14]([O-])([OH:16])=[O:15].O>C(OC(=O)C)(=O)C.C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N+:14]([O-:16])=[O:15])=[C:7]2[C:12]=1[C:11](=[O:13])[CH2:10][CH2:9][CH2:8]2

참가 물질

6

반응물 3

HCID 944Nitric AcidHCID 962WaterHCID 112753358-Methoxy-3,4-dihydronaphthalen-1(2H)-one

생성물 1

HCID 111720678-methoxy-5-nitro-3,4-dihydro-1(2H)-naphthalenone

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 7918Acetic Anhydride용매

반응 조건

온도
0 °C

실험 절차

A solution of 8-methoxy-1-tetralone (2.26 g, 13 mmol) (prepared as described in Chatterjee, A. Tetrahedron, (1980), 36, 2513-2520) in acetic anhydride (11.5 mL) was cooled to 0° C., treated with a mixture of fuming nitric acid (0.90 mL) in acetic acid (0.70 mL) dropwise over 1 hour, stirred at 0° C. for 1.5 hours, treated with water (150 mL) and extracted with diethyl ether (300 mL). The diether ether layer was washed with water (150 mL), washed with sodium bicarbonate solution (3×), washed with brine, dried (MgSO4), filtered and concentrated. Purification of the residue on silica gel using a gradient of 2:1 and then 3:2 and finally 1:1 hexanes:ethyl acetate provided the desired product as the more polar isomer.

후처리

  1. extractionextracted with diethyl ether (300 mL)
  2. washThe diether ether layer was washed with water (150 mL)
  3. washwashed with sodium bicarbonate solution (3×)
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification of the residue on silica gel using a gradient of 2:1

출처 및 근거

ORD 기록
ord-170144955c944271a0017f417eb4653c
출처 데이터셋
uspto-grants-2003_01
특허 번호
US06503935B1

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