Hydrochloric Acid → HCID 13704246, compound

HRID 1916290Notes

Reaction equation

HRID 1916290 reaction equation
[CH2:1]([O:3][C:4](=[O:8])[CH2:5][C:6]#[N:7])[CH3:2].[H-].[Na+].[CH3:11][O:12][C:13](=[O:24])[C:14]1[CH:19]=[CH:18][C:17](F)=[C:16]([N+:21]([O-:23])=[O:22])[CH:15]=1.Cl>CN(C=O)C.C(OCC)(=O)C>[CH3:11][O:12][C:13](=[O:24])[C:14]1[CH:19]=[CH:18][C:17]([CH:5]([C:6]#[N:7])[C:4]([O:3][CH2:1][CH3:2])=[O:8])=[C:16]([N+:21]([O-:23])=[O:22])[CH:15]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7764Ethyl cyanoacetateHCID 24758Sodium hydrideHCID 5219721Methyl 4-fluoro-3-nitrobenzoate

Product 1

HCID 13704246HCID 13704246, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

Ethylcyanoacetate (1.14 g, 10.0 mmol, 2 eq) in 1 mL DMF was added at 0° C. to a suspension of sodium hydride (0.4 g, 60% in mineral oil, 5.02 mmol) in 3 mL DMF under an atmosphere of nitrogen. The reaction mixture was stirred at room temperature for 30 minutes before the dropwise addition of 4-fluoro-3-nitro-benzoic acid methyl ester (1.05 g, 22.7 mmol) in 5 mL DMF. After stirring for 2 hours at room temperature, 2 M HCl (20 mL) and ethyl acetate (20 mL) were added to the red solution. The organic layer was washed with water and brine, dried over sodium sulphate and concentrated to give the title compound as an orange oil, which was used without further purification (1.47 g, 5.03 mmol). 1H NMR (CDCl3) δ 8.83 (1H, d, J=1.5), 8.38 (1H, dd, J=8.0, 1.8), 7.89 (1H, d, J=8.1), 5.74 (1H, s), 4.30 (2H, q, J=7.1), 4.00 (3H, s), 1.32 (3H, t, J=7.0).

Workup

  1. washThe organic layer was washed with water and brine
  2. dry with materialdried over sodium sulphate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-9e2343b29484498f8940faafeb8be8ee
Source dataset
uspto-grants-2013_12
Patent number
US08618121B2

Reaction notes

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