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

HRID 2295504노트

반응식

HRID 2295504 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 21735183Dimethylformamide toluene용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-d344e76115ee423abf113cc2c2ceba0d
출처 데이터셋
uspto-grants-1984_01
특허 번호
US04425350

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