HCID 13580544, compound → HCID 13520523, compound

HRID 1380581Notes

Reaction equation

HRID 1380581 reaction equation
[CH2:1]([C:3]1[C:7]([C:8]2[NH:9][C:10]3[C:15]([C:16]=2[C:17](=O)[CH2:18][CH2:19][C:20]([N:22]([CH3:24])[CH3:23])=O)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[C:6]([CH3:26])[O:5][N:4]=1)[CH3:2]>C1COCC1>[CH2:1]([C:3]1[C:7]([C:8]2[NH:9][C:10]3[C:15]([C:16]=2[CH2:17][CH2:18][CH2:19][CH2:20][N:22]([CH3:23])[CH3:24])=[CH:14][CH:13]=[CH:12][CH:11]=3)=[C:6]([CH3:26])[O:5][N:4]=1)[CH3:2]

Participants

3

Reactant 1

HCID 13580544HCID 13580544, compound

Product 1

HCID 13520523HCID 13520523, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 5.3 grams (0.015 mole) of 2-(3-ethyl-5-methyl-4-isoxazolyl)-N,N-dimethyl-γ-oxo-indole-3-butanamide in 75 ml dry THF is added dropwise to a refluxing suspension of 1.71 grams (0.045 mole) of LiAlH and 50 ml THF. The mixture is refluxed 2 hours after addition and then cooled and quenched by the addition of ethyl acetate, 2N sodium hydroxide and water. The mixture is filtered and the THF evaporated. The residue is dissolved in CH2Cl2, washed with water, dried over MgSO4, filtered and evaporated. The residue is dissolved in ether and converted to the hydrochloride salt with gaseous HCl giving the title compound as the hydrochloride, m.p. 155.5°-157.5° C.

Workup

  1. temperatureThe mixture is refluxed 2 hours
  2. additionafter addition
  3. temperaturecooled
  4. customquenched by the addition of ethyl acetate, 2N sodium hydroxide and water
  5. filtrationThe mixture is filtered
  6. customthe THF evaporated
  7. dissolutionThe residue is dissolved in CH2Cl2
  8. washwashed with water
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. customevaporated
  12. dissolutionThe residue is dissolved in ether

Sources & evidence

ORD record
ord-98fca20e874c4f41ad2bb234dca59596
Source dataset
uspto-grants-1986_04
Patent number
US04582848

Reaction notes

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