Methanol → HCID 15744974, compound

HRID 327474Notes

Reaction equation

HRID 327474 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 to 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-3787d82bb3984e249f5736bba5073c93
Source dataset
uspto-grants-1993_12
Patent number
US05273975

Reaction notes

Loading…