HCID 20379978, compound → HCID 20379968, compound

HRID 1448489Notes

Reaction equation

HRID 1448489 reaction equation
[CH3:1][C:2]1([CH3:25])[C:6]2=[N:7][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[C:14]([NH:15][CH2:16][CH2:17][CH2:18][N:19]3[CH2:23][CH2:22][CH2:21][C:20]3=O)=[C:5]2[CH2:4][O:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O1CCCC1>O1CCCC1>[CH3:1][C:2]1([CH3:25])[C:6]2=[N:7][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[C:14]([NH:15][CH2:16][CH2:17][CH2:18][N:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)=[C:5]2[CH2:4][O:3]1

Participants

5

Reactant 3

HCID 20379978HCID 20379978, compoundHCID 21226445Aluminium lithium hydrideHCID 21881883Oxolane--water (1/1)

Product 1

HCID 20379968HCID 20379968, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1,3-dihydro-3,3-dimethyl-9-[[3-(2-oxo-1-pyrrolidinyl)propyl]amino]-furo[3,4-b]quinoline (9.5 g, described in Example 36) in tetrahydrofuran (150 ml) is slowly added to a mixture of lithium aluminum hydride (9.5 g) in tetrahydrofuran (600 ml). The mixture is heated at reflux for 3 hours and cooled. A solution of water-tetrahydrofuran (1:1) is added dropwise and the mixture is filtered. The filtrate is evaporated and a mixture of water-chloroform is added to the residue. The organic phase is separated, dried and evaporated. The residue is subjected to chromatography on a column of alumina (activity II) using acetone-benzene (3:7) as eluant. Evaporation of the eluates and crystallization of the residual oil gives the title compound, mp 70°-75° C. Treatment of the title compound with a solution of hydrogen chloride in ether gives the hydrochloride salt of the title compound, mp 170°-175° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 3 hours
  3. temperaturecooled
  4. filtrationthe mixture is filtered
  5. customThe filtrate is evaporated
  6. additiona mixture of water-chloroform
  7. additionis added to the residue
  8. customThe organic phase is separated
  9. customdried
  10. customevaporated
  11. customEvaporation of the eluates and crystallization of the residual oil

Sources & evidence

ORD record
ord-794a18eb2aef46bab31d32634092126a
Source dataset
uspto-grants-1979_12
Patent number
US04180580

Reaction notes

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