Water → HCID 21463487, compound

HRID 1940598Notes

Reaction equation

HRID 1940598 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:11](=[O:17])[CH:12]=[CH:13][N:14]([CH3:16])[CH3:15])[C:5]2[O:9][CH2:8][CH2:7][C:6]=2[CH:10]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[NH2:1][C:2]1[CH:3]=[C:4]([C:11](=[O:17])[CH2:12][CH2:13][N:14]([CH3:16])[CH3:15])[C:5]2[O:9][CH2:8][CH2:7][C:6]=2[CH:10]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 54289347HCID 54289347, compound

Product 1

HCID 21463487HCID 21463487, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1-(5-amino-2,3-dihydrobenzofuran-7-yl)-3-dimethylamino- propene-1-one (D14) (400 mg) in dry tetrahydrofuran (9 ml) was added to a stirred suspension of lithium aluminium hydride (46 mg) in dry tetrahydrofuran (9 ml) at 0° C. under argon. The mixture was stirred at this temperature for 1/4 h then treated sequentially with water (0.046 ml), 10% NaOH (0.068 ml) and water (0.12 ml). After a further 1/4 h stirring at room temperature the mixture was filtered through kieselguhr, and washed with dry tetrahydrofuran, and the solvent was evaporated under reduced pressure to give the title compound as a yellow/orange solid (352 mg, 87%).

Workup

  1. stirringAfter a further 1/4 h stirring at room temperature the mixture
  2. filtrationwas filtered through kieselguhr
  3. washwashed with dry tetrahydrofuran
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-725fd748274b403689a5972b17a51746
Source dataset
uspto-grants-1997_12
Patent number
US05700818

Reaction notes

Loading…