Iodoethane → HCID 21961374, compound

HRID 887620Notes

Reaction equation

HRID 887620 reaction equation
[CH3:1][C:2]1([CH3:15])[C:11]2[C:6](=[CH:7][C:8]([N+:12]([O-:14])=[O:13])=[CH:9][CH:10]=2)[NH:5][CH2:4][CH2:3]1.I[CH2:17][CH3:18].[H-].[Na+]>CN(C=O)C>[CH2:17]([N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[CH:7]=2)[C:2]([CH3:15])([CH3:1])[CH2:3][CH2:4]1)[CH3:18]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 219614774,4-Dimethyl-7-nitro-1,2,3,4-tetrahydroquinoline

Product 1

HCID 21961374HCID 21961374, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The mixture of 4,4-dimethyl-7-nitro-1,2,3,4-tetrahydro-quinoline (0.48 g, 2.33 mmol), iodoethane (0.21 ml, 2.56 mmol), and NaH (60%, 0.10 g, 2.5 mmol) in 10 ml of DMF was stirred at RT overnight, and partitioned between EtOAc and H2O. The combined organic portions were washed with brine, dried with MgSO4, filtered, and condensed. The crude compound was purified by flash column chromatography (5 to 10% of CH2Cl2 in hexanes). The titled compound was obtained as a yellow oil. MS (ES+): 235.3 (M+H)+. Calc'd for C13H18N2O2—234.29.

Workup

  1. custompartitioned between EtOAc and H2O
  2. washThe combined organic portions were washed with brine
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. customcondensed
  6. customThe crude compound was purified by flash column chromatography (5 to 10% of CH2Cl2 in hexanes)

Sources & evidence

ORD record
ord-f7ad1619255b4cfb84fad662ff0d5574
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

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