Benzene → (1Z,2E)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-[(3,4,5-trimethoxyphenyl)methylene]-2-[3-(3,4,5-trimethoxyphenyl)-1-oxo-2-propenyl]isoquinoline

HRID 597145

反応式

HRID 597145 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][C:15]([OH:17])=O)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].C1C=CC=CC=1.C(N(CC)C#CC)C.[CH3:32][O:33][C:34]1[CH:35]=[C:36]2[C:41](=[CH:42][C:43]=1[O:44][CH3:45])[C:40](=[CH:46][C:47]1[CH:52]=[C:51]([O:53][CH3:54])[C:50]([O:55][CH3:56])=[C:49]([O:57][CH3:58])[CH:48]=1)[NH:39][CH2:38][CH2:37]2>N1C=CC=CC=1>[CH3:32][O:33][C:34]1[CH:35]=[C:36]2[C:41](=[CH:42][C:43]=1[O:44][CH3:45])/[C:40](=[CH:46]/[C:47]1[CH:52]=[C:51]([O:53][CH3:54])[C:50]([O:55][CH3:56])=[C:49]([O:57][CH3:58])[CH:48]=1)/[N:39]([C:15](=[O:17])/[CH:14]=[CH:13]/[C:5]1[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)[CH2:38][CH2:37]2

参加物

6

反応物 4

HCID 241BenzeneHCID 70213-(3,4,5-Trimethoxyphenyl)acrylic acidHCID 77909N,N-Diethyl-1-propyn-1-amineHCID 706389523,4-Dihydro-6,7-dimethoxy-1-[(3,4,5-trimethoxyphenyl)methylene]isoquinoline

生成物 1

HCID 21446881(1Z,2E)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-[(3,4,5-trimethoxyphenyl)methylene]-2-[3-(3,4,5-trimethoxyphenyl)-1-oxo-2-propenyl]isoquinoline

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

To a solution of 100 parts of 3-(3,4,5-trimethoxyphenyl)-2-propenoic acid in 1125 parts of benzene is added 22 parts of N,N-diethyl-1-propyne-1-amine. The resultant mixture is stirred for 2 hours, whereupon a solution of 75 parts of 3,4-dihydro-6,7-dimethoxy-1-[(3,4,5-trimethoxyphenyl)methylene]isoquinoline [Ber. deut. chem. Ges., 55, 2889 (1922)] in 200 parts of pyridine is introduced. The mixture thus obtained is stirred and heated at 65° for 3 hours, then cooled, consecutively washed with water and aqueous 5% sodium bicarbonate, dried over anhydrous sodium sulfate, and stripped of solvent by vacuum distillation. The residue is crystallized from a mixture of ethyl acetate and ether to give (1Z,2E)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-[(3,4,5-trimethoxyphenyl)methylene]-2-[3-(3,4,5-trimethoxyphenyl)-1-oxo-2-propenyl]isoquinoline melting at 180°-183°.

後処理

  1. additionis introduced
  2. customThe mixture thus obtained
  3. temperatureheated at 65° for 3 hours
  4. temperaturecooled
  5. washconsecutively washed with water and aqueous 5% sodium bicarbonate
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationstripped of solvent by vacuum distillation
  8. customThe residue is crystallized from a mixture of ethyl acetate and ether

出典と根拠

ORDレコード
ord-a65d5414117c49ab875f8c002918072d
出典データセット
uspto-grants-1977_03
特許番号
US04013644

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