Methanol → HCID 20331060, compound

HRID 2057659Notes

Reaction equation

HRID 2057659 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][NH:29][C:30]2[CH:37]=[CH:36][C:33]([C:34]#N)=[CH:32][CH:31]=2)=[CH:15][CH:14]=1.C[OH:39]>C1(C)C=CC=CC=1>[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][NH:29][C:30]2[CH:37]=[CH:36][C:33]([CH:34]=[O:39])=[CH:32][CH:31]=2)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 20331289HCID 20331289, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 20331060HCID 20331060, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Di-isobutylaluminum hydride (54 ml., 25% solution in toluene) is added with stirring to a solution of 12.1 g. of 4-[10-(4-methoxyphenyl)decylamino]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 separted. The aqueous solution is extracted twice with toluene (100 ml.) and the combined organic layers are washed with aqueous 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 dichloromethane/hexanes 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. extractionThe aqueous solution is extracted twice with toluene (100 ml.)
  6. washthe combined organic layers are washed with aqueous sodium bicarbonate
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customto give a light yellow crystalline solid
  11. customThe product is recrystallized from dichloromethane/hexanes giving colorless needles

Sources & evidence

ORD record
ord-9788f0524f6648e69a0a7e20984e2ac0
Source dataset
uspto-grants-1980_07
Patent number
US04211783

Reaction notes

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