HCID 19861151, compound → HCID 12877973, compound

HRID 2308701Notes

Reaction equation

HRID 2308701 reaction equation
[N:1]1([CH:6]([CH2:16][CH2:17][CH2:18][CH3:19])[C:7]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)=[O:8])[CH:5]=[N:4][CH:3]=[N:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[N:1]1([CH:6]([CH2:16][CH2:17][CH2:18][CH3:19])[CH:7]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[OH:8])[CH:5]=[N:4][CH:3]=[N:2]1

Participants

4

Reactant 2

HCID 19861151HCID 19861151, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 12877973HCID 12877973, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The product (0.01 mol) of Stage 2 was added portionwise to a suspension of lithium aluminium hydride (0.005 mol) in diethyl ether (10 ml; dried over sodium) to maintain refluxing. The ethereal solution was refluxed for a further four hours; the excess lithium aluminium hydride was quenched with water (20.0 ml) and the mixture acidified with concentrated sulphuric acid. The ethereal layer was washed with water (4×25 ml) and dried over anhydrous sodium sulphate. Removal of the ether gave an oil which solidified on standing. Recrystallisation from methylene chloride/petroleum ether gave the title compound as a white solid, m.p. 93°-94°.

Workup

  1. temperatureto maintain
  2. temperaturerefluxing
  3. temperatureThe ethereal solution was refluxed for a further four hours
  4. customthe excess lithium aluminium hydride was quenched with water (20.0 ml)
  5. washThe ethereal layer was washed with water (4×25 ml)
  6. dry with materialdried over anhydrous sodium sulphate
  7. customRemoval of the ether
  8. customgave an oil which
  9. customRecrystallisation from methylene chloride/petroleum ether

Sources & evidence

ORD record
ord-72ec75b9fd12409e84f0ac8ae6e17733
Source dataset
uspto-grants-1987_09
Patent number
US04690941

Reaction notes

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