Potassium Carbonate → 2-(2-Fluoroethyl)-6-(methyloxy)-7-nitro-1,2,3,4-tetrahydroisoquinoline

HRID 1014367Notes

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[CH2:17][CH2:18][F:19].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[F:19][CH2:18][CH2:17][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

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 1-iodo-2-fluoroethane (0.40 g, 2.3 mmol) and potassium carbonate (500 mg, 3.62 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, and concentrated to provide 2-(2-fluoroethyl)-6-(methyloxy)-7-nitro-1,2,3,4-tetrahydroisoquinoline which was taken directly to the next step without determination of yield. 1H NMR (400 MHz, CDCl3) δ ppm 2.89-3.04 (m, 6 H), 3.77 (s, 2 H), 3.94 (s, 3 H), 4.62-4.80 (dt, JHF=47.6, J=4.6 Hz, 2 H), 6.82 (s, 1 H), 7.63 (s, 1 H); ESIMS (M+H)+=255.

Workup

temperaturecooled
custompartitioned between ethyl acetate and water
customThe organic layer was separated
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-8f6ec317af264a4dac5465050650dd63
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07981903B2

Reaction notes

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