Methylamine → 2-Benzoyl-3-methylaminocrotononitrile

HRID 2051628Notes

Reaction equation

HRID 2051628 reaction equation
[CH3:1][NH2:2].C([Li])CCC.[C:8](/[C:16](=[C:19](/OC)\[CH3:20])/[C:17]#[N:18])(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>>[C:8](/[C:16](=[C:19](/[NH:2][CH3:1])\[CH3:20])/[C:17]#[N:18])(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 3

HCID 6329MethylamineHCID 234685002-Benzoyl-3-methoxycrotononitrileHCID 178418339Butyllithium

Product 1

HCID 234685252-Benzoyl-3-methylaminocrotononitrile

Procedure

In the glass liner of a stainless steel bomb cooled to -78° is condensed 10 ml. of methylamine. To this is added 0.5 ml. of 2 M n-butyllithium (in hexane), followed by 5.0 g. of 2-benzoyl-3-methoxycrotononitrile. The bomb is sealed and heated on a steam bath overnight. The bomb is then cooled, opened and the contents evaporated. The residue is dissolved in chloroform, passed through a Magnesol® pad and the filtrate is evaporated. The residue is recrystallized from chloroform-hexane yielding the title compound.

Workup

  1. customcondensed 10 ml
  2. additionTo this is added 0.5 ml
  3. customThe bomb is sealed
  4. temperatureheated on a steam bath overnight
  5. temperatureThe bomb is then cooled
  6. customthe contents evaporated
  7. dissolutionThe residue is dissolved in chloroform
  8. customthe filtrate is evaporated
  9. customThe residue is recrystallized from chloroform-hexane yielding the title compound

Sources & evidence

ORD record
ord-fe8cbf89a45f49edb4113ca84e483a10
Source dataset
uspto-grants-1980_01
Patent number
US04181677

Reaction notes

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