Sodium Hydroxide → HCID 22661968, compound

HRID 392905Notes

Reaction equation

HRID 392905 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[C:6]([CH:9]=1)[C:7]#[N:8].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>C1COCC1>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][CH2:12][N:13]2[CH2:14][CH2:15][O:16][CH2:17][CH2:18]2)=[C:6]([CH:9]=1)[CH2:7][NH2:8]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 22661944HCID 22661944, compound

Product 1

HCID 22661968HCID 22661968, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-chloro-2-(2-morpholin-4-yl-ethoxy)benzonitrile (412 mg, 1.54 mmol) in anhydrous THF (15 mL) was added to a solution of lithium aluminum hydride (3.53 mL, 1.0 M in THF) at room temperature. The reaction was stirred for 15 h at room temperature under anhydrous conditions, whereupon it was cooled to 0° C. and 1 N aqueous NaOH (0.54 mL) was added. The reaction was stirred for ½ h at 0° C. and then the solids were filtered off and rinsed with THF. The filtrate was concentrated by rotary evaporation and the resulting solid was dissolved in 30 mL of absolute ethanol. Aqueous hydrochoride solution (1.0 N, 1.7 mL) was added and the reaction was stirred for 15 min. The solvent was removed by rotary evaporation and the resulting solid was triturated with Et2O to to yield the title compound.

Workup

  1. temperaturewas cooled to 0° C.
  2. stirringThe reaction was stirred for ½ h at 0° C.
  3. filtrationthe solids were filtered off
  4. washrinsed with THF
  5. concentrationThe filtrate was concentrated by rotary evaporation
  6. dissolutionthe resulting solid was dissolved in 30 mL of absolute ethanol
  7. additionAqueous hydrochoride solution (1.0 N, 1.7 mL) was added
  8. stirringthe reaction was stirred for 15 min
  9. customThe solvent was removed by rotary evaporation
  10. customthe resulting solid was triturated with Et2O

Sources & evidence

ORD record
ord-9caf9dcd3f58425ebe86915f33c9597d
Source dataset
uspto-grants-2004_10
Patent number
US06803457B1

Reaction notes

Loading…