2,6-Dichlorobenzaldehyde → 1-(2,6-Dichlorostyryl)-6,7-dimethoxyisoquinoline

HRID 1419817

反応式

HRID 1419817 の反応式
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[CH:5]=[CH:4][N:3]=1.[Cl:16][C:17]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[C:18]=1[CH:19]=O.C(OC(=O)C)(=O)C>CCOCC>[Cl:16][C:17]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[C:18]=1[CH:19]=[CH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[CH:5]=[CH:4][N:3]=1

参加物

5

反応物 3

HCID 67372,6-DichlorobenzaldehydeHCID 7918Acetic AnhydrideHCID 207256,7-Dimethoxy-1-methylisoquinoline

生成物 1

HCID 539377371-(2,6-Dichlorostyryl)-6,7-dimethoxyisoquinoline収率 79%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

A mixture of 20.4 g (0.1 mole) of 1-methyl-6,7-dimethoxyisoquinoline, 18.9 g (0.108 mole) of 2,6-dichlorobenzaldehyde and 15 ml of acetic anhydride is stirred in an oil bath of 150°-160° C. for 3 hours. The termination of the reaction is controlled by thin layer chromatography. The reaction mixture is cooled to a temperature between 5° C. and 10° C. under stirring, 30 ml of ether are added to it, the separated crystals are filtered and washed twice with cold ether. The thus-obtained raw product is recrystallized from a mixture of 600 ml of acetone and 130 ml of water, The clarified solution is stirred at a temperature between 0° C. and 5° C. for 2 hours, the separated substance is filtered, washed with 25 ml of a 6:1.3 mixture of 0° C. acetone and water and dried. Thus 28.4 g (79%) of 1-(2,6-dichlorostyryl)-6,7-dimethoxyisoquinoline are obtained.

後処理

  1. temperatureThe reaction mixture is cooled to a temperature between 5° C. and 10° C.
  2. stirringunder stirring
  3. filtrationthe separated crystals are filtered
  4. washwashed twice with cold ether
  5. customThe thus-obtained raw product
  6. customis recrystallized from a mixture of 600 ml of acetone and 130 ml of water
  7. stirringThe clarified solution is stirred at a temperature between 0° C. and 5° C. for 2 hours
  8. filtrationthe separated substance is filtered
  9. washwashed with 25 ml of a 6:1.3 mixture of 0° C. acetone and water
  10. customdried

出典と根拠

ORDレコード
ord-22b9b265aaae4ddbada5102082efc57e
出典データセット
uspto-grants-1999_03
特許番号
US05889018

関連ノート

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