HCID 15479546, compound → HCID 23291913, compound

HRID 365511Notes

Reaction equation

HRID 365511 reaction equation
[CH:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([NH2:14])=[CH:11][CH:12]=2)[C:7]([CH3:16])([CH3:15])[CH2:6][C:5]1=O)([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([NH2:14])=[CH:11][CH:12]=2)[C:7]([CH3:16])([CH3:15])[CH2:6][CH2:5]1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 15479546HCID 15479546, compound2×HCID 21226445Aluminium lithium hydride

Product 1

HCID 23291913HCID 23291913, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

(1-Isopropyl-4,4-dimethyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)amine (Compound 1, 1.3 g, 5.6 mmol) was dissolved in tetrahydrofuran (80 mL) and the solution was cooled to 0° C. under argon. The solution was treated with 1M lithium aluminum hydride (15.0 mL, 15.0 mmol) and the reaction stirred at 0° C. to room temperature for 16 hours. The reaction was cooled to 0° C., poured onto ice and extracted with ether (2×). The combined organic extracts were washed with brine and dried (MgSO4). The filtered solution was concentrated under reduced pressure and the crude product was purified by silica gel chromatography (5% ethyl acetate in hexanes) to give the title compound as an oil.

Workup

  1. temperatureThe reaction was cooled to 0° C.
  2. additionpoured onto ice
  3. extractionextracted with ether (2×)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationThe filtered solution was concentrated under reduced pressure
  7. customthe crude product was purified by silica gel chromatography (5% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-be1129408686490b9580ee43f48d79df
Source dataset
uspto-grants-2000_10
Patent number
US06127382

Reaction notes

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