Trimethylphenylammonium hydroxide → (+/-)-5,6,6a,7-tetrahydro-2,3,9,10-tetramethoxy-5-methyl-4H-dibenz(de,g)isoquinoline

HRID 2295504ノート

反応式

HRID 2295504 の反応式
[OH:1][C:2]1[C:3]([O:24][CH3:25])=[CH:4][C:5]2[C:14]3[CH:15]=[C:16]([O:21][CH3:22])[C:17]([O:19][CH3:20])=[CH:18][C:13]=3[CH2:12][CH:11]3[C:6]=2[C:7]=1[CH2:8][N:9]([CH3:23])[CH2:10]3.[OH-].[C:27]1([N+](C)(C)C)C=CC=CC=1>C1(C)C=CC=CC=1.CN(C)C=O>[CH3:25][O:24][C:3]1[C:2]([O:1][CH3:27])=[C:7]2[CH2:8][N:9]([CH3:23])[CH2:10][CH:11]3[CH2:12][C:13]4[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[CH:15][C:14]=4[C:5](=[C:6]23)[CH:4]=1

参加物

4

反応物 2

HCID 15913Trimethylphenylammonium hydroxideHCID 12802079(+/-)-5,6,6a,7-Tetrahydro-3-hydroxy-2,9,10-trimethoxy-5-methyl-4H-dibenz(de,g)isoquinoline

生成物 1

HCID 12802085(+/-)-5,6,6a,7-tetrahydro-2,3,9,10-tetramethoxy-5-methyl-4H-dibenz(de,g)isoquinoline

試薬・触媒・溶媒 1

HCID 21735183Dimethylformamide toluene溶媒

実験手順

9.1 g. (±)-5,6,6a,7-Tetrahydro-3-hydroxy-2,9,10-trimethoxy-5-methyl-4H-dibenz(de,g)isoquinoline (see Example 2) are reacted with phenyltrimethylammonium hydroxide in toluene/dimethylformamide in a manner analogous to that described in Example 7. When the methylation is finished, the reaction mixture is worked up in the manner described in Example 7. By chromatography of the crude product on silica gel (elution with chloroform +1% triethylamine) and crystallisation from chloroform-diethyl ether, there is obtained (±)-5,6,6a,7-tetrahydro-2,3,9,10-tetramethoxy-5-methyl-4H-dibenz(de,g)isoquinoline in the form of beige crystals; m.p. 170°-177° C.

後処理

  1. customBy chromatography of the crude product on silica gel (elution with chloroform +1% triethylamine) and crystallisation from chloroform-diethyl ether

出典と根拠

ORDレコード
ord-d344e76115ee423abf113cc2c2ceba0d
出典データセット
uspto-grants-1984_01
特許番号
US04425350

反応ノート

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