Iodoethane → HCID 42597541, compound

HRID 1014296Notes

Reaction equation

HRID 1014296 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]2.C(=O)([O-])[O-].[K+].[K+].I[CH2:20][CH3:21]>CN(C=O)C>[CH2:20]([O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]2)[CH3:21]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 27740406-Hydroxy-3,4-dihydro-2(1H)-quinolinone

Product 1

HCID 42597541HCID 42597541, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To 6-hydroxy-3,4-dihydro-2(1 H)-quinolinone (90.2 g, 0.55 mol, 1 equiv) in DMF (1.8 L) was added potassium carbonate (228 g, 1.65 mol, 3 equiv). The slurry was stirred for 45 min. at 25° C., then iodoethane (114 g, 0.73 mol, 1.33 equiv) was added and stirring was continued for 12 hours. The mixture was filtered, the filtrate was poured into water, and the white precipitate was collected via filtration, washed with water (500 mL), and dried under high vacuum to provide 6-(ethyloxy)-3,4-dihydro-2(1H)-quinolinone (72.3 g, 69%). 1H NMR (400 MHz, DMSO) δ, 1.25 (t, J=7.2 Hz, 3H), 2.35 (m, 2 H), 2.78 (m, 2H), 3.90(m, 2H), 6.70-6.73 (m, 3H), 9.83 (br, 1H).

Workup

  1. stirringstirring
  2. waitwas continued for 12 hours
  3. filtrationThe mixture was filtered
  4. additionthe filtrate was poured into water
  5. filtrationthe white precipitate was collected via filtration
  6. washwashed with water (500 mL)
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-67ca9b39d3ee4eb6be07a81c9b9fc788
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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