Hydrochloric Acid → 3-(Quinolin-6-yl)propanal

HRID 1966369Notes

Reaction equation

HRID 1966369 reaction equation
C([O:3][CH:4](OCC)[CH2:5][CH2:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]=[CH:12][CH:11]=[CH:10]2)C.Cl>C(OCC)(=O)C>[N:13]1[C:14]2[C:9](=[CH:8][C:7]([CH2:6][CH2:5][CH:4]=[O:3])=[CH:16][CH:15]=2)[CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 579711766-(3,3-Diethoxypropyl)quinoline

Product 1

HCID 229313103-(Quinolin-6-yl)propanalYield 100%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
2.5 °C

Procedure

A solution of 6-(3,3-diethoxypropyl)quinoline (23, Method A of Example 16, 520 g , 2.08 mol, 1.0 equiv) in ethyl acetate (EtOAc, 2.2 L) was cooled to 0° C. before a 2 N aqueous hydrochloric acid (HCl) solution (2.2 L) was added over 1 h while keeping the reaction temperature below 5° C. The resulting reaction mixture was stirred for an additional 2 h at 0-5° C. When TLC and HPLC/MS indicated the reaction was complete, the reaction was quenched with an ice cold 3 N aqueous sodium hydroxide (NaOH) solution at 0° C. until the pH was between 8 to 9. The layers were separated and the aqueous layer was extracted with ethyl acetate (EtOAc, 2 L). The combined organic layers were washed with brine (2 L), dried with sodium sulfate (Na2SO4), and concentrated under the reduced pressure to afford crude 3-(quinolin-6-yl)propanal (9, 385.3 g, 385.3 g theoretical, 100%) as a yellow oil, which was found to be identical to the material obtained from Method 1 in every comparable aspect. Since this crude material was found to be sufficiently pure, it was used directly in subsequent reaction without further purification.

Workup

  1. additionwas added over 1 h
  2. customthe reaction temperature below 5° C
  3. customThe resulting reaction mixture
  4. customthe reaction was quenched with an ice cold 3 N aqueous sodium hydroxide (NaOH) solution at 0° C. until the pH
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with ethyl acetate (EtOAc, 2 L)
  7. washThe combined organic layers were washed with brine (2 L)
  8. dry with materialdried with sodium sulfate (Na2SO4)
  9. concentrationconcentrated under the reduced pressure

Sources & evidence

ORD record
ord-1ae77c13a6144e2986676ebe4d771986
Source dataset
uspto-grants-2013_04
Patent number
US08420645B2

Reaction notes

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