Diethyl Ether → HCID 19012251, compound

HRID 1729240Notes

Reaction equation

HRID 1729240 reaction equation
[C:1]1([C:7]2[C:12]3[N:13]4[C:22]5[C:17](=[CH:18][CH:19]=[CH:20][C:21]=5[C:11]=3[CH:10]=[C:9]([C:23](OCC)=[O:24])[N:8]=2)[CH2:16][CH2:15][CH2:14]4)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].CCOCC.[OH-].[Na+]>O1CCCC1.O>[C:1]1([C:7]2[C:12]3[N:13]4[C:22]5[C:17](=[CH:18][CH:19]=[CH:20][C:21]=5[C:11]=3[CH:10]=[C:9]([CH2:23][OH:24])[N:8]=2)[CH2:16][CH2:15][CH2:14]4)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 19012243HCID 19012243, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19012251HCID 19012251, compoundYield 75.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.4 g (4 mmol) of 8-phenyl-10-ethoxycarbonyl-5,6-dihydro-4H-pyrido[4',3':4,5]pyrrolo[3,2,1-ij]quinoline were dissolved in 25 ml of tetrahydrofuran and added dropwise to a mixture of 0.5 g (13 mmol) of lithium aluminium hydride and 10 ml of ether at a temperature of 30° C. After cooling, 1 ml of water and 1 ml of 2N sodium hydroxide solution were added dropwise successively. After boiling for 15 minutes the solid was filtered off. The filtrate was evaporated in vacuum. The residue was boiled with 20 ml of ethanol and kept at 0° C. for 24 hours. The solid was sucked off and dried. Obtained were 0.95 g of the desired product having a melting-point of 209°-211° C.

Workup

  1. temperatureAfter cooling
  2. filtrationthe solid was filtered off
  3. customThe filtrate was evaporated in vacuum
  4. waitkept at 0° C. for 24 hours
  5. customdried
  6. customObtained

Sources & evidence

ORD record
ord-d368025df6084cc781490cc053e4cfdd
Source dataset
uspto-grants-1994_07
Patent number
US05332746

Reaction notes

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