Aluminium lithium hydride → HCID 22079771, compound

HRID 1900759Notes

Reaction equation

HRID 1900759 reaction equation
[CH:1]([NH:3][CH2:4][CH:5]1[O:19][C:8]2=[C:9]3[C:14](=[C:15]([CH3:17])[CH:16]=[C:7]2[CH2:6]1)[NH:13][C:12](=[O:18])[CH:11]=[CH:10]3)=O.[H-].[Li+].[Al+3].[H-].[H-].[H-]>O1CCCC1>[CH3:17][C:15]1[CH:16]=[C:7]2[CH2:6][CH:5]([CH2:4][NH:3][CH3:1])[O:19][C:8]2=[C:9]2[C:14]=1[NH:13][C:12](=[O:18])[CH:11]=[CH:10]2

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 23369729(+)-2-Formylaminomethyl-5-methyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-one

Product 1

HCID 22079771HCID 22079771, compoundYield 82.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

(+)-2-Formylaminomethyl-5-methyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-one (460 mg, 1.78 mM) was dissolved in dry tetrahydrofuran (100 ml). To the solution, aluminum lithium hydride (135 mg, 3.57 mM) was added thereto. The mixture was dried while stirring in a bath of 50° C. in the atmosphere of nitrogen for 18 hours. The reaction mixture was cooled. A small amount of ethyl acetate was added. The solvent was distilled off under reduced pressure. 2N-caustic soda solution was added to the residue, followed by extraction with a solvent mixture of chloroform: methanol=10:1. The extract was dried, and the solvent was distilled off under reduced pressure. 360 mg of the title compound was obtained as a crude (+)-5-methyl-2-methylaminomethyl-2,3,6,7-tetrahydrofuro [2,3-f]quinoline-7-one (82.9%). The obtained crude was dissolved in methanol. 4N-HCl in 1,4-dioxane solution (0.4 ml) was added to the methanol solution of the crude, and the solution was concentrated. The resultant concentrate was recrystallized from methanol--ether, obtaining 276 mg of the title compound (66.7%) as yellow powder.

Workup

  1. customThe mixture was dried
  2. temperatureThe reaction mixture was cooled
  3. additionA small amount of ethyl acetate was added
  4. distillationThe solvent was distilled off under reduced pressure
  5. addition2N-caustic soda solution was added to the residue
  6. extractionfollowed by extraction with a solvent mixture of chloroform
  7. customThe extract was dried
  8. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-e442d5d5f7804b42ad35ffb85ddc5a3b
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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