Ammonia → HCID 15379780, compound

HRID 1451277Notes

Reaction equation

HRID 1451277 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH:9]([CH3:11])[NH2:10].Cl[C:13]1[C:18]([C:19]#[N:20])=[CH:17][CH:16]=[CH:15][N:14]=1.N>CN(C)C(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH:9]([NH:10][C:13]1[C:18]([C:19]#[N:20])=[CH:17][CH:16]=[CH:15][N:14]=1)[CH3:11]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 810792-ChloronicotinonitrileHCID 10910315172699-35-3

Product 1

HCID 15379780HCID 15379780, compoundYield 41.4%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2,6-dichloro-α-methylbenzenemethanamine (0.03 mol) and 2-chloro-3-pyridinecarbonitrile (0.03 mol) in N,N-dimethylacetamide (few drops) was stirred for 20 hours at 90° C. The reaction mixture was cooled and poured out into aqueous ammonia. The mixture was extracted twice with CH2Cl2. The organic layer was separated, washed with water, dried (MgSO4), filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /hexane 50/50). The pure fractions were collected and the solvent was evaporated, yielding 3.6 g (±)-2-[[1-(2,6-dichlorophenyl)ethyl]amino]-3-pyridinecarbonitrile (41.4%); mp. 84.4° C. (comp. 9).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionThe mixture was extracted twice with CH2Cl2
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /hexane 50/50)
  9. customThe pure fractions were collected
  10. customthe solvent was evaporated

Sources & evidence

ORD record
ord-81bf21130bf14791ab12109c9ef11df3
Source dataset
uspto-grants-1997_02
Patent number
US05604230

Reaction notes

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