Hydrochloric Acid → NSC248834

HRID 2175368Notes

Reaction equation

HRID 2175368 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][CH:11]=[C:12]([C:16]#[N:17])[CH2:13][C:14]#[N:15].[O-]CC.[Na+].Cl>C(O)C>[O:2]=[C:3]1[C:4]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:10]2[CH:11]=[C:12]([C:16]#[N:17])[CH:13]=[C:14]2[NH:15]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2723922Sodium ethoxideHCID 78042725HCID 78042725, compound2×

Product 1

HCID 317322NSC248834Yield 97.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Under cooling on ice, in a solution of 2-(2,3-dicyanopropen-1-ylamino)benzoic acid methyl ester (E isomer/Z isomer mixture) (Reference Compound 2-1, 40.1 g, 0.166 mol) in ethanol (700 mL), a solution of sodium ethoxide (28.2 g, 0.414 mol) in ethanol (300 mL) was added dropwise. After stirring the reaction solution at room temperature for 2 hours, 1M hydrochloric acid (500 mL) was added under cooling on ice. The precipitated solid was collected by filtration, and washed with water. By drying under reduced pressure, the title Reference Compound (33.8 g, yield: 97%) was obtained as a colorless powder (see Z. Chem. 1961, 1, 349).

Workup

  1. temperatureunder cooling on ice
  2. filtrationThe precipitated solid was collected by filtration
  3. washwashed with water
  4. customBy drying under reduced pressure

Sources & evidence

ORD record
ord-4155269555ad40ea83a0999f70deaf45
Source dataset
uspto-grants-2015_06
Patent number
US09062061B2

Reaction notes

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