Dimethylformamide → 1-Isopropyl-1,2,3,4-tetrahydroquinoline-2-carbaldehyde

HRID 1263467Notes

Reaction equation

HRID 1263467 reaction equation
P(Cl)(Cl)(Cl)=O.CN(C)[CH:8]=[O:9].[CH:11]([N:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:17][CH2:16][CH2:15]1)([CH3:13])[CH3:12].C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.CCCCCC>[CH:11]([N:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:17][CH2:16][CH:15]1[CH:8]=[O:9])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 155556251-Isopropyl-1,2,3,4-tetrahydroquinoline

Product 1

HCID 224936131-Isopropyl-1,2,3,4-tetrahydroquinoline-2-carbaldehydeYield 56.2%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Phosphorus oxychloride (18.6 g) was added dropwise to 29.2 g of N,N-dimethylformamide under ice cooling. The resulting mixture was stirred at room temperature for 30 minutes, followed by the dropwise addition of 17.5 g of 1-isopropyl-1,2,3,4-tetrahydroquinoline slowly under ice cooling. After stirring at room temperature for one hour, the reaction mixture was poured into ice water, neutralized with a saturated aqueous solution of sodium bicarbonate and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue so obtained was subjected to chromatography on a silica gel column (developing solvent: 10% ethyl acetate/n-hexane), whereby 11.4 g of the title compound were obtained as a reddish brown oil.

Workup

  1. stirringAfter stirring at room temperature for one hour
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue so obtained

Sources & evidence

ORD record
ord-f8b8c08f35ec4233afb2ef410962d5c2
Source dataset
uspto-grants-2003_04
Patent number
US06541474B2

Reaction notes

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