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

HRID 1582871ノート

反応式

HRID 1582871 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 313Hydrochloric Acid溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-fec3dca9695c4b5bb0a64db93ce728f7
出典データセット
uspto-grants-2004_05
特許番号
US06740650B2

反応ノート

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