Ethanol → HCID 12833329, compound

HRID 1065286Notes

Reaction equation

HRID 1065286 reaction equation
[CH3:1][NH:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][CH:7]=[N:6][C:5]=1[CH:10]=[C:11](N)[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1.[O:21]1CCCC1.C(O)C.[OH-].[Na+]>O.C(O)(=O)C>[CH3:1][NH:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][CH:7]=[N:6][C:5]=1[CH2:10][C:11](=[O:21])[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 86738367HCID 86738367, compound2×

Product 1

HCID 12833329HCID 12833329, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

22 g. (76.5 mmol.) of 2-(4'-chloro-β-aminostyryl)nicotinic acid N-methylamide (Compound XIX) were dissolved in 80 ml. of tetrahydrofuran and 40 ml. of ethanol and a mixture of 40 ml. of acetic acid and 40 ml. of water was added. The reaction mixture was stirred at 40° C. for 4 hours. The reaction mixture was then made basic to pH 9 with sodium hydroxide solution and extracted with diethyl ether, ethyl acetate and methylene chloride. The three organic extracts were combined, treated with charcoal, dried over anhydrous magnesium sulfate and concentrated at reduced pressure to obtain a yellow solid which was recrystallized from ethanol to obtain the product as a yellow green solid, m.p. 162°-163° C.

Workup

  1. extractionextracted with diethyl ether, ethyl acetate and methylene chloride
  2. additiontreated with charcoal
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated at reduced pressure
  5. customto obtain a yellow solid which
  6. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-b5222bbff40245f3a00c25170ca13bd0
Source dataset
uspto-grants-1982_05
Patent number
US04329349

Reaction notes

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