Hydrochloric Acid → HCID 68520592, compound

HRID 1916284Notes

Reaction equation

HRID 1916284 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:10])[CH2:7][C:8]#[N:9])[CH3:4].F[C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][C:13]=1[N+:20]([O-:22])=[O:21].Cl>CN(C=O)C.C(OCC)(=O)C>[CH2:3]([O:5][C:6](=[O:10])[CH:7]([C:8]#[N:9])[C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][C:13]=1[N+:20]([O-:22])=[O:21])[CH3:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7764Ethyl cyanoacetateHCID 24758Sodium hydrideHCID 27746544-Fluoro-3-nitrobenzonitrile

Product 1

HCID 68520592HCID 68520592, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of sodium hydride (0.96 g, 60% in mineral oil, 24 mmol) in DMF (6 mL) at 0° C. was added ethylcyanoacetate (2.72 g, 24 mmol) in DMF (2 mL) under an atmosphere of nitrogen. The reaction mixture was stirred at room temperature for 30 minutes then 4-fluoro-3-nitro-benzonitrile (2.05 g, 22.7 mmol) in DMF (5 mL) was added dropwise. 1M HCl and ethyl acetate were added to the reaction mixture after 1 hour. The organic layer was washed with water and brine, then dried over sodium sulphate and concentrated to give a brown oil which was purified by flash column chromatography to give the title compound. 1H NMR (DMSO-d6) δ 8.79 (1H), 8.38 (1H), 7.95 (1H, d, J=2), 6.38 (1H), 4.21 (2H), 1.19 (3H, t).

Workup

  1. washThe organic layer was washed with water and brine
  2. dry with materialdried over sodium sulphate
  3. concentrationconcentrated
  4. customto give a brown oil which
  5. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-f4687d2c5d7940dc8f6584c2465dea5e
Source dataset
uspto-grants-2013_12
Patent number
US08618121B2

Reaction notes

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