Iodoethane → HCID 67027655, compound

HRID 1505935Notes

Reaction equation

HRID 1505935 reaction equation
[CH2:1]([I:3])[CH3:2].[CH3:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[C:14]([O:16][CH3:17])[CH:15]=1)[CH:12]=[N:11][CH2:10][CH2:9]2>C(#N)C>[I-:3].[CH2:10]([N+:11]1[CH2:2][CH2:1][C:8]2[C:13](=[C:14]([O:16][CH3:17])[CH:15]=[C:6]([O:5][CH3:4])[CH:7]=2)[CH:12]=1)[CH3:9]

Participants

4

Reactant 2

HCID 6340IodoethaneHCID 12582374HCID 12582374, compound

Product 1

HCID 67027655HCID 67027655, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Ethyl iodide (0.6 mL, 7.32 mmol) was added to a solution of 6,8-dimethoxy-3,4-dihydroisoquinoline (700 mg, 3.66 mmol) in acetonitrile (15 mL) and the mixture was left to stir in the dark for 20 h. The resultant precipitate was collected by filtration, washed with acetonitrile and left to air dry to afford the title compound as a yellow solid (750 mg, 95%). 1H NMR (CD3OD, 300 MHz): 8.96 (s, 1H), 6.63 (d, J=2.2 Hz, 1H), 6.61 (d, J=2.2 Hz, 1H), 4.02-3.88 (m, 7H), 3.18 (t, J=7.9 Hz, 2H), 2.03 (s, 5H), 1.47 (t, J=7.3 Hz, 3H).

Workup

  1. waitthe mixture was left
  2. filtrationThe resultant precipitate was collected by filtration
  3. washwashed with acetonitrile
  4. waitleft to air
  5. customdry

Sources & evidence

ORD record
ord-033573bdab8b4dfc9b18560b69fb810d
Source dataset
uspto-grants-2015_12
Patent number
US09216980B2

Reaction notes

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