Ethyl Bromide → 2-Ethyl-4,4-dimethyl-7-nitro-1,2,3,4-tetrahydroisoquinoline

HRID 2370640Notes

Reaction equation

HRID 2370640 reaction equation
Br[CH2:2][CH3:3].[CH3:4][C:5]1([CH3:18])[C:14]2[C:9](=[CH:10][C:11]([N+:15]([O-:17])=[O:16])=[CH:12][CH:13]=2)[CH2:8][NH:7][CH2:6]1.C([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[CH2:2]([N:7]1[CH2:6][C:5]([CH3:18])([CH3:4])[C:14]2[C:9](=[CH:10][C:11]([N+:15]([O-:17])=[O:16])=[CH:12][CH:13]=2)[CH2:8]1)[CH3:3]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 219596554,4-Dimethyl-7-nitro-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 681946722-Ethyl-4,4-dimethyl-7-nitro-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Bromoethane (0.75 g, 6.88 mmol) was added to a solution of 4,4-dimethyl-7-nitro-1,2,3,4-tetrahydroisoquinoline (1.4 g, 6.79 mmol) and K2CO3 (2 g, 14.47 mmol) in N,N-dimethylformamide (80 mL). The mixture was stirred at 50° C. for 4 hours. The solvent was removed under vacuum to give a residue which was purified by silica gel column chromatography eluting with 10% ethyl acetate/heptane to provide the title compound.

Workup

  1. customThe solvent was removed under vacuum
  2. customto give a residue which
  3. customwas purified by silica gel column chromatography
  4. washeluting with 10% ethyl acetate/heptane

Sources & evidence

ORD record
ord-dcd39920ca334990b39ee8d8febd2b69
Source dataset
uspto-grants-2014_04
Patent number
US08710065B2

Reaction notes

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