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Iodoethane → 1-Ethyl-6-methoxy-2-oxo-1,2,3,4-tetrahydro-quinoline-7-carbaldehyde

HRID 1243982
Notes
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Reaction equation

HRID 1243982 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[CH:13]=[O:14])[NH:9][C:8](=[O:15])[CH2:7][CH2:6]2.[CH3:16][C:17](C)([O-])C.[K+].C(I)C>C1COCC1.C(=O)(O)[O-].[Na+]>[CH2:16]([N:9]1[C:10]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[C:12]([CH:13]=[O:14])[CH:11]=2)[CH2:6][CH2:7][C:8]1=[O:15])[CH3:17]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 101251496-Methoxy-2-oxo-1,2,3,4-tetrahydro-quinoline-7-carbaldehydeHCID 23665647Potassium tert-butoxide

Product 1

HCID 219317301-Ethyl-6-methoxy-2-oxo-1,2,3,4-tetrahydro-quinoline-7-carbaldehyde

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent
HCID 516892
Sodium Bicarbonate
Solvent

Conditions

Temperature
0 °C

Procedure

6-Methoxy-2-oxo-1,2,3,4-tetrahydro-quinoline-7-carbaldehyde (preparation 3) 60 mg (0.293 mmol) was dissolved in 5 ml of anhydrous THF and the solution was cooled to 0° C. The reaction mixture was treated with 33 mg (0.293 mmol) of potassium t-butoxide whereupon it became yellow in color. After stirring for 30 minutes, the mixture was treated with 23 μl (0.293 mmol) ethyl iodide and slowly warmed to room temperature while stirring for 16 hours (h). The reaction mixture was diluted with saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate. The organic phase was dried over sodium sulfate and concentrated to an oil. The residue was chromatographed on silica gel eluting with 6/4 ethyl acetate/hexane to afford 34 mg (40%) as a white solid. MS APCI m/e 234 (p+1)

Workup

  1. temperatureslowly warmed to room temperature
  2. stirringwhile stirring for 16 hours (h)
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. concentrationconcentrated to an oil
  6. customThe residue was chromatographed on silica gel eluting with 6/4 ethyl acetate/hexane
  7. customto afford 34 mg (40%) as a white solid

Sources & evidence

ORD record
ord-038ec84659ca4c1caba32b2f8fe6b238
Source dataset
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07119207B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes