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

HRID 1451660

반응식

HRID 1451660 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-e3a50547f5614d08b31602d8cef265af
출처 데이터셋
uspto-grants-1997_02
특허 번호
US05604237

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