Ammonia → HCID 15379780, compound

HRID 374592Notes

Reaction equation

HRID 374592 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: CH2C2 /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: CH2C2 /hexane 50/50)
  9. customThe pure fractions were collected
  10. customthe solvent was evaporated

Sources & evidence

ORD record
ord-6c63651933b141e9a16054345db1f324
Source dataset
uspto-grants-1996_01
Patent number
US05480997

Reaction notes

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