Methanol → HCID 15744974, compound

HRID 1648317Notes

Reaction equation

HRID 1648317 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:10]([CH2:24][CH2:25][CH3:26])[CH:11]1[CH2:20][C:19]2[C:14](=[C:15]([O:21][CH3:22])[CH:16]=[CH:17][CH:18]=2)[NH:13][C:12]1=O)[CH2:8][CH3:9].C(OCC)(=O)C.CO>C1COCC1>[CH3:22][O:21][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:14]=1[NH:13][CH2:12][CH:11]([N:10]([CH2:7][CH2:8][CH3:9])[CH2:24][CH2:25][CH3:26])[CH2:20]2

Participants

6

Reactant 4

HCID 887MethanolHCID 8857Ethyl AcetateHCID 15744973HCID 15744973, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 15744974HCID 15744974, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Lithium aluminum hydride (1.08 g, 27.7 mmol) was added to a stirred solution of 3-(dipropylamino)-3,4-dihydro-8-methoxy-2(1H)quinolinone (1.05 g, 3.8 mmol) in THF (50 mL) and the solution was heated at 50° C. for 1 hour. After cooling, ethyl acetate followed by methanol were added to destroy excess hydride, and the solvent was evaporated. The residue was partitioned between ethyl acetate and water. Evaporation of the ethyl acetate gave 0.98 g of 1,2,3,4-tetrahydro-8-methoxy-N,N-dipropyl-3-quinolinamine as an oil.

Workup

  1. temperatureAfter cooling
  2. additionwere added
  3. customto destroy excess hydride
  4. customthe solvent was evaporated
  5. customThe residue was partitioned between ethyl acetate and water
  6. customEvaporation of the ethyl acetate

Sources & evidence

ORD record
ord-71c1b04e784d4232a05d30003d9b766d
Source dataset
uspto-grants-1995_07
Patent number
US05436240

Reaction notes

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