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

HRID 1014369Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 65 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-16391d0078e64887a16058cc92a774e6
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07981903B2

Reaction notes

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