Sodium Hydroxide → HCID 131715104, compound

HRID 542855Notes

Reaction equation

HRID 542855 reaction equation
[Cl-:1].[Al+3].[Cl-].[Cl-].[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:11][O:12][C:13]1[CH:14]=[C:15]2[C:20](=[C:21]([NH:23][C:24](=O)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][N:30]3[CH2:35][CH2:34][S:33][CH2:32][CH2:31]3)[CH:22]=1)[N:19]=[CH:18][CH:17]=[C:16]2[CH3:37].[OH-].[Na+]>O1CCCC1.O>[ClH:1].[ClH:1].[CH3:11][O:12][C:13]1[CH:14]=[C:15]2[C:20](=[C:21]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][N:30]3[CH2:31][CH2:32][S:33][CH2:34][CH2:35]3)[CH:22]=1)[N:19]=[CH:18][CH:17]=[C:16]2[CH3:37]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 13077521HCID 13077521, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 131715104HCID 131715104, compoundYield 120.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

To 50 ml of tetrahydrofuran at -50° was added 2.7 g (0.02 mole) of anhydrous aluminum chloride. The slurry was added to a mixture of 2.2 g (0.058 mole) of lithium aluminum hydride in 100 ml of tetrahydrofuran at -30° and the mixture was stirred and allowed to warm to -20°. A solution of 5.6 g (0.0144 mole) of N-(6-methoxy-4-methyl-8-quinolinyl)-4-thiamorpholine-hexanamide in 50 ml of tetrahydrofuran was added to the mixture dropwise. The mixture was stirred at -10° for 3 hr, allowed to warm to room temperature and treated with 9.2 ml of 30% sodium hydroxide and 150 ml of water. The mixture was filtered through celite and concentrated to dryness in vacuo. The residual oil was chromatographed over 200 g of silica gel first with ethyl acetate and then with 2% methanol in ethyl acetate. The eluant containing product, Rf(silica gel--ethyl acetate)=0.17, was concentrated and the residual oil was taken up in 2-propanol and treated with excess of a saturated solution of hydrogen chloride in 2-propanol. The resulting precipitate was collected, washed with 2-propanol and dried in vacuo at 60° to afford 5.4 g (82%) of the title compound, mp 257°-259° (dec). The presence of 2-propanol was confirmed by NMR spectroscopy.

Workup

  1. temperatureto warm to -20°
  2. stirringThe mixture was stirred at -10° for 3 hr
  3. filtrationThe mixture was filtered through celite and
  4. concentrationconcentrated to dryness in vacuo
  5. customThe residual oil was chromatographed over 200 g of silica gel first with ethyl acetate
  6. additionThe eluant containing product, Rf(silica gel--ethyl acetate)=0.17
  7. concentrationwas concentrated
  8. additiontreated with excess of a saturated solution of hydrogen chloride in 2-propanol
  9. customThe resulting precipitate was collected
  10. washwashed with 2-propanol
  11. customdried in vacuo at 60°

Sources & evidence

ORD record
ord-e62ca225ba0f4be88619eec9aa9e3c45
Source dataset
uspto-grants-1987_04
Patent number
US04659708

Reaction notes

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