Hydrochloric Acid → HCID 13147347, compound

HRID 1916298Notes

Reaction equation

HRID 1916298 reaction equation
[CH2:1]([O:3][C:4](=[O:8])[CH2:5][C:6]#[N:7])[CH3:2].[H-].[Na+].[N+:11]([C:14]1[CH:15]=[N:16][CH:17]=[CH:18][C:19]=1Cl)([O-:13])=[O:12].Cl>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:8])[CH:5]([C:6]#[N:7])[C:19]1[CH:18]=[CH:17][N:16]=[CH:15][C:14]=1[N+:11]([O-:13])=[O:12])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7764Ethyl cyanoacetateHCID 24758Sodium hydrideHCID 27357814-Chloro-3-nitropyridine

Product 1

HCID 13147347HCID 13147347, compoundYield 64.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

Ethylcyanoacetate (3.75 g, 38 mmol) in 3 mL DMF was added dropwise at 0° C. to a suspension of sodium hydride (1.5 g, 60% in mineral oil, 38 mmol) in DMF (9 mL). The reaction mixture was stirred at room temperature for 30 minutes then cooled to ° C. and 3-nitro-4-chloropyridine (2.63 g, 19 mmol, 1 eq) in DMF (3 mL) added slowly. 2 M HCl (20 mL) and ethyl acetate (20 mL) were added after 2 hours stirring at room temperature and the organic layer was washed with water and brine, before being dried over sodium sulphate and concentrated to give a red/orange oil. The crude oil was triturated with ethyl acetate and the resultant solid collected by filtration to give the title compound (2.88 g, 48%). 1H NMR (d6-DMSO) δ 13.2 (s, br), 8.70 (1H, s), 7.88 (1H, dd, J=7.1, 1.0), 4.06 (2H, q, J=7.1), 1.18 (3H, t, J=7.1); LC-MS (1) Rt 1.13 min; m/z (ES−) 190, 234.

Workup

  1. temperaturethen cooled
  2. stirringstirring at room temperature
  3. washthe organic layer was washed with water and brine
  4. dry with materialbefore being dried over sodium sulphate
  5. concentrationconcentrated
  6. customto give a red/orange oil
  7. customThe crude oil was triturated with ethyl acetate
  8. filtrationthe resultant solid collected by filtration

Sources & evidence

ORD record
ord-32fb76c7461641ce8cf37af3d134b57e
Source dataset
uspto-grants-2013_12
Patent number
US08618121B2

Reaction notes

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