Water → 2,3-Dimethoxy-8,9-methylenedioxy-dibenzo[c,h]cinnoline

HRID 1582871노트

반응식

HRID 1582871 반응식
[NH2:1][C:2]1[CH:7]=[C:6]2[O:8][CH2:9][O:10][C:5]2=[CH:4][C:3]=1[C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[CH:17]=[C:16]([O:21][CH3:22])[C:15]([O:23][CH3:24])=[CH:14]2.[N:25]([O-])=O.[Na+].O.C(OCC)(=O)C>C(O)(=O)C.Cl>[CH3:22][O:21][C:16]1[C:15]([O:23][CH3:24])=[CH:14][C:13]2[C:18]([CH:17]=1)=[CH:19][CH:20]=[C:11]1[C:12]=2[N:25]=[N:1][C:2]2[CH:7]=[C:6]3[O:8][CH2:9][O:10][C:5]3=[CH:4][C:3]1=2

참가 물질

7

반응물 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 227164376-(2-Amino-4,5-methylenedioxyphenyl)-2,3-dimethoxy-naphthaleneHCID 23668193Sodium Nitrite

생성물 1

HCID 99057072,3-Dimethoxy-8,9-methylenedioxy-dibenzo[c,h]cinnoline수율 50%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 313Hydrochloric Acid용매

실험 절차

6-(2-Amino-4,5-methylenedioxyphenyl)-2,3-dimethoxy-naphthalene (13, 40 mg, 0.13 mmol) in acetic acid (2 mL) and concentrated hydrochloric acid (0.3 mL) was cooled to 0° C. and diazotised with a solution of sodium nitrite (0.09 g in 1.5 mL water). The diazonium solution was allowed to rise slowly to room temperature and left overnight. Water (50 mL) was added to the red solution with some precipitate. The resulting mixture was extracted with ethyl acetate, washed with diluted sodium hydroxide solution, then with water, dried (anhydrous Na2SO4) and rotaevaporated to give the crude product. Chromatography on silica gel using 40:60 hexanes:ethyl acetate afforded the title compound (20 mg) in 50% yield; 1H NMR (CDCl3) d 4.09(3H, s), 4.22(3H, s), 6.24(2H, s), 7.31(1H, s), 7.80(1H s), 7.95(1H, s), 8.00(1H, d, J=9.2), 8.13(1H, d, J=8.9), 9.14(1H, s); 13C NMR d 56.5 56.9, 98.1, 102.9, 104.6, 107.5, 107.9, 117.1, 119.6, 120.6, 126.8, 128.5, 131.7, 141.9, 145.6, 150.2, 151.2, 152.1.

후처리

  1. customto rise slowly to room temperature
  2. extractionThe resulting mixture was extracted with ethyl acetate
  3. washwashed with diluted sodium hydroxide solution
  4. dry with materialwith water, dried (anhydrous Na2SO4)
  5. customto give the crude product

출처 및 근거

ORD 기록
ord-fec3dca9695c4b5bb0a64db93ce728f7
출처 데이터셋
uspto-grants-2004_05
특허 번호
US06740650B2

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