Hydrochloric Acid → HCID 10446445, compound

HRID 1030630Notes

Reaction equation

HRID 1030630 reaction equation
[C:1]([C:4]1[CH:9]=CC=C[N:5]=1)(=O)C.[C-]#N.[Na+].[OH-].[NH4+:14].Cl.C([N:18]([CH2:21][CH3:22])[CH2:19][CH3:20])C.[C:23](Cl)(=[O:32])[C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1.[CH3:34]O>O.CCOCC>[C:9]([C:4]([NH:5][C:23](=[O:32])[C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1)([C:21]1[CH:22]=[CH:34][CH:20]=[CH:19][N:18]=1)[CH3:1])#[N:14]

Participants

10

Reactant 7

HCID 313Hydrochloric AcidHCID 887Methanol2×HCID 7477p-Anisoyl chlorideHCID 8471TriethylamineHCID 8929Sodium CyanideHCID 142862-AcetylpyridineHCID 14923Ammonium Hydroxide

Product 1

HCID 10446445HCID 10446445, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
50 °C

Procedure

2-Acetylpyridine (10.0 g, 0.0825 mole) was added to 50° C. solution of sodium cyanide (4.0 g, 0.0825 mole) ammonium chloride (4.9 g, 0.0908 mole), and ammonium hydroxide (2.9 g, 0.0825 mole ) in water (22 mL) and methanol (15 mL). The resulting mixture was stirred at 50° C. overnight. The mixture was cooled and concentrated under reduced pressure. The residue was dissolved in methylene chloride (40 mL) and washed with water (10 mL) and dried over MgSo4. Filtration and concentration gave a dark red oil which was dissolved in methanol and treated with saturated ethereal HCl. Concentration yielded a low melting solid which was dissolved in tetrahydrofurna (50 mL) and treated sequentially with triethylamine (13.7 g, 0.135 mole) and p-anisoyl chloride (8.4 g, 0.0495 mole) dropwise. The solution was stirred 3 hours at room temperature then diluted with ether (100 mL) and washed with 2M HCl, 1M NaOH, saturated NaCl, and dried over MgSo4. Filtration and concentration of the solvent in vacuo provided a solid which was recrystalized from ethyl acetate/hexane to give 5.2 g of N-[-1-cyano-1-(2-pyridinyl)ethyl]-4-methoxybenzamide, mp 173° C.

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in methylene chloride (40 mL)
  4. washwashed with water (10 mL)
  5. customdried over MgSo4
  6. filtrationFiltration and concentration
  7. customgave a dark red oil which
  8. concentrationConcentration
  9. customyielded a low melting solid which
  10. dissolutionwas dissolved in tetrahydrofurna (50 mL)
  11. stirringThe solution was stirred 3 hours at room temperature
  12. washwashed with 2M HCl, 1M NaOH, saturated NaCl
  13. customdried over MgSo4
  14. filtrationFiltration and concentration of the solvent in vacuo
  15. customprovided a solid which
  16. customwas recrystalized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-097cc6906ab44ba79329e516a37430bc
Source dataset
uspto-grants-1992_04
Patent number
US05106873

Reaction notes

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