Methanol → HCID 20498904, compound

HRID 128329Notes

Reaction equation

HRID 128329 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[CH:11]1([NH:17][C:18]2[CH:25]=[CH:24][C:21]([C:22]#N)=[CH:20][CH:19]=2)[CH2:16][CH2:15][CH:14]=[CH:13][CH2:12]1.C[OH:27]>C1(C)C=CC=CC=1>[CH:11]1([NH:17][C:18]2[CH:25]=[CH:24][C:21]([CH:22]=[O:27])=[CH:20][CH:19]=2)[CH2:16][CH2:15][CH:14]=[CH:13][CH2:12]1

Participants

5

Reactant 3

HCID 887MethanolHCID 20499010HCID 20499010, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 20498904HCID 20498904, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Di-isobutylaluminium hydride (54 ml., 25% solution in toluene) is added with stirring to a solution of 12.1 g. of 4-(cyclohex-3-enylamino)benzonitrile under a nitrogen atmosphere. After addition is completed, the solution stirred for one hour. A solution of methanol in toluene (50 ml., 1:1) is added over 30 minutes and the mixture is poured into 500 ml. vigorously stirred ice-cold 50% aqueous sulfuric acid. The mixture is filtered and the organic layer separated. The aqueous solution is extracted twice with toluene (100 ml.) and the combined organic layers are washed with acqueous sodium bicarbonate, dried over magnesium sulfate, decolorized with charcoal, filtered and evaporated in vacuo to give a light yellow crystalline solid. The product is recrystallized from dicloromethane/hexane giving colorless needles.

Workup

  1. additionAfter addition
  2. stirringthe solution stirred for one hour
  3. additionthe mixture is poured into 500 ml
  4. filtrationThe mixture is filtered
  5. customthe organic layer separated
  6. extractionThe aqueous solution is extracted twice with toluene (100 ml.)
  7. washthe combined organic layers are washed with acqueous sodium bicarbonate
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customevaporated in vacuo
  11. customto give a light yellow crystalline solid
  12. customThe product is recrystallized from dicloromethane/hexane giving colorless needles

Sources & evidence

ORD record
ord-f5f77c0ac46647e683c84a177da5d586
Source dataset
uspto-grants-1981_03
Patent number
US04259352

Reaction notes

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