Potassium Carbonate → 1,2,3,4-Tetrahydro-6,7,8-trimethoxy-2-[2-(4-nitrophenyl)ethyl]isoquinoline

HRID 1451660

反応式

HRID 1451660 の反応式
Br[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1.[CH3:13][O:14][C:15]1[CH:16]=[C:17]2[C:22](=[C:23]([O:27][CH3:28])[C:24]=1[O:25][CH3:26])[CH2:21][NH:20][CH2:19][CH2:18]2.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:13][O:14][C:15]1[CH:16]=[C:17]2[C:22](=[C:23]([O:27][CH3:28])[C:24]=1[O:25][CH3:26])[CH2:21][N:20]([CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1)[CH2:19][CH2:18]2

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 792664-Nitrophenethyl bromideHCID 1927231,2,3,4-Tetrahydro-6,7,8-trimethoxyisoquinoline

生成物 1

HCID 199745401,2,3,4-Tetrahydro-6,7,8-trimethoxy-2-[2-(4-nitrophenyl)ethyl]isoquinoline収率 61.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 1-(2-bromoethyl)-4-nitrobenzene (0.34 g), 1,2,3,4-tetrahydro-6,7,8-trimethoxyisoquinoline [0.33 g; J. Chem. Soc. D, (20), 1296-1297 (1970)] and potassium carbonate (0.5 g) in DMF (20 ml) was heated at 50° for 12 h. The mixture was then filtered and the filtrate evaporated. The residue was taken up in water, extracted with dichloromethane, dried, evaporated and purified by column chromatography eluting with dichloromethane/methanol (99:1) to give the title compound (0.34 g) as a red solid, MP: 110°. NMR includes signals at d 3.55 (2H,s,N--CH2Ar), 3.70 (6H,s,OCH3), 3.75 (3H,s,OCH3).

後処理

  1. temperaturewas heated at 50° for 12 h
  2. filtrationThe mixture was then filtered
  3. customthe filtrate evaporated
  4. extractionextracted with dichloromethane
  5. customdried
  6. customevaporated
  7. custompurified by column chromatography
  8. washeluting with dichloromethane/methanol (99:1)

出典と根拠

ORDレコード
ord-e3a50547f5614d08b31602d8cef265af
出典データセット
uspto-grants-1997_02
特許番号
US05604237

関連ノート

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