Ammonium Hydroxide → HCID 18378553, compound

HRID 2298819Notes

Reaction equation

HRID 2298819 reaction equation
[NH:1]1[C:7](=O)[CH2:6][CH2:5][CH2:4][C:3]2[CH:9]=[CH:10][N:11]=[CH:12][C:2]1=2.[H-].[Al+3].[Li+].[H-].[H-].[H-].[H-].[OH-].[NH4+]>O1CCCC1>[NH:1]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]2[CH:9]=[CH:10][N:11]=[CH:12][C:2]1=2

Participants

6

Reactant 4

HCID 14923Ammonium HydroxideHCID 166653HydrideHCID 18378674HCID 18378674, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18378553HCID 18378553, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2,3,4,5-tetrahydro-1H-pyrido[3,4-b]azepin-2-one (470 mg) in tetrahydrofuran (20 ml) was treated with lithium aluminum hydride (990 mg) and stirred at room temperature for 30 minutes. The excess hydride was decomposed with 28% ammonium hydroxide at 0° C. The resulting mixture was filtered through a bed of Celite and the Celite was washed with tetrahydrofuran, and the filtrate was concentrated. The residual aqueous layer was extracted with chloroform, dried over sodium sulfate, concentrated and purified by silica gel column chromatography (SiO2; 20 g, 1% methanol in chloroform) to give 2,3,4,5-tetrahydro-1H-pyrido[3,4-b]azepine (370 mg).

Workup

  1. filtrationThe resulting mixture was filtered through a bed of Celite
  2. washthe Celite was washed with tetrahydrofuran
  3. concentrationthe filtrate was concentrated
  4. extractionThe residual aqueous layer was extracted with chloroform
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. custompurified by silica gel column chromatography (SiO2; 20 g, 1% methanol in chloroform)

Sources & evidence

ORD record
ord-244ca721b99744a59cacfe30bd146b4a
Source dataset
uspto-grants-2002_12
Patent number
US06495542B1

Reaction notes

Loading…