Aluminium lithium hydride → HCID 68226750, compound

HRID 1952552Notes

Reaction equation

HRID 1952552 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH:7]1[C:15]2[C:10](=[C:11]([CH2:16][CH2:17][C:18]#[N:19])[CH:12]=[CH:13][CH:14]=2)[CH:9]=[N:8]1>C1COCC1>[NH:7]1[C:15]2[C:10](=[C:11]([CH2:16][CH2:17][CH2:18][NH2:19])[CH:12]=[CH:13][CH:14]=2)[CH:9]=[N:8]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68226809HCID 68226809, compound

Product 1

HCID 68226750HCID 68226750, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of the 1.0M LAH in THF (8.3 mL, 8.30 mmol) at 0° C. was added drop wise a solution of 3-(1H-Indazol-4-yl)-propionitrile (0.94 g, 5.491 mmol) in anhydrous THF (20 mL) over 3 min. The resultant reaction mixture was gradually warmed and stirred at room temp for 2 h. The reaction was quenched by cooling in an ice bath followed by adding aq. 1N NaOH (1 mL). The suspension was filtered through celite, washed well with THF, concentrated and extracted with 3/1: EtOAc/THF. The organic layer were washed with brine (20 mL). The organic layer washed with brine (50 mL), dried over anhydrous magnesium sulfate, filtered, concentrated give 3-(1H-Indazol-4-yl)-propylamine (684.1 mg, 71.1%) as a pale yellow oil. MS m/e 173.3 (M+H+). This was taken to next step.

Workup

  1. customThe resultant reaction mixture
  2. temperaturewas gradually warmed
  3. customThe reaction was quenched
  4. temperatureby cooling in an ice bath
  5. additionby adding aq. 1N NaOH (1 mL)
  6. filtrationThe suspension was filtered through celite
  7. washwashed well with THF
  8. concentrationconcentrated
  9. extractionextracted with 3/1
  10. washThe organic layer were washed with brine (20 mL)
  11. washThe organic layer washed with brine (50 mL)
  12. dry with materialdried over anhydrous magnesium sulfate
  13. filtrationfiltered
  14. concentrationconcentrated

Sources & evidence

ORD record
ord-c2fe85f817dc467d9880b3eb50a4039d
Source dataset
uspto-grants-2013_03
Patent number
US08404859B2

Reaction notes

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