Isopropyl iodide → 2-(1-Methylethyl)-6-(methyloxy)-7-nitro-1,2,3,4-tetrahydroisoquinoline

HRID 1014369노트

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HRID 1014369 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[CH2:9][NH:8][CH2:7][CH2:6]2.I[CH:17]([CH3:19])[CH3:18].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:18][CH:17]([N:8]1[CH2:7][CH2:6][C:5]2[C:10](=[CH:11][C:12]([N+:13]([O-:15])=[O:14])=[C:3]([O:2][CH3:1])[CH:4]=2)[CH2:9]1)[CH3:19]

참가 물질

5

반응물 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 594418746-Methoxy-7-nitro-1,2,3,4-tetrahydroisoquinoline

생성물 1

HCID 594416842-(1-Methylethyl)-6-(methyloxy)-7-nitro-1,2,3,4-tetrahydroisoquinoline수율 89.6%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
65 °C

실험 절차

6-(methyloxy)-7-nitro-1,2,3,4-tetrahydroisoquinoline (222 mg, 1.07 mmol) was taken in acetonitrile (5 mL), treated with 2-iodopropane (0.8 mL, 5.0 mmol) and potassium carbonate (600 mg, 4.35 mmol, Aldrich). The mixture was heated at 65° C. for 16 h, cooled, and partitioned between ethyl acetate and water. The organic layer was separated, dried over magnesium sulfate, filtered, concentrated, and purified by chromatography on SiO2 (0 to 20% methanol/dichloromethane spiked with aqueous ammonia) to provide 2-(1-methylethyl)-6-(methyloxy)-7-nitro-1,2,3,4-tetrahydro isoquinoline (0.24 g, 88%). 1H NMR (400 MHz, CDCl3) δ ppm 1.16 (d, J=6.4 Hz, 6 H), 2.76-2.84 (m, 2 H), 2.90-3.00 (m, 3 H), 3.70 (s, 2 H), 3.93 (s, 3 H), 6.80 (s, 1 H), 7.64 (s, 1 H); ESIMS (M+H)+=251.

후처리

  1. temperaturecooled
  2. custompartitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by chromatography on SiO2 (0 to 20% methanol/dichloromethane spiked with aqueous ammonia)

출처 및 근거

ORD 기록
ord-16391d0078e64887a16058cc92a774e6
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07981903B2

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