Acetic Acid → HCID 178468759, compound

HRID 2121351Notes

Reaction equation

HRID 2121351 reaction equation
[NH2:1][C:2]1[C:12]([NH2:13])=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].C(O)(=O)C.[N:18]1[CH:23]=[CH:22][C:21]([CH:24]=O)=[CH:20][CH:19]=1.Cl.O.[S-2].[Na+].[Na+]>C(O)C.O.S([O-])([O-])(=O)=O.[Cu+2]>[N:18]1[CH:23]=[CH:22][C:21]([C:24]2[NH:1][C:2]3[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:9][CH:10]=[CH:11][C:12]=3[N:13]=2)=[CH:20][CH:19]=1

Participants

9

Reactant 5

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 133894-PyridinecarboxaldehydeHCID 11171330Ethyl 2,3-diaminobenzoateHCID 19906495Sodium sulfide monohydrate

Product 1

HCID 178468759HCID 178468759, compoundYield 78.2%

Reagents, catalysts & solvents 3

HCID 24462Copper SulfateCatalystHCID 702EthanolSolvent2×HCID 962WaterSolvent2×

Conditions

Temperature
50 °C

Procedure

1 g (5.5 mmol) of ethyl 2,3-diaminobenzoate and 0.7 ml (11.3 mmol) of acetic acid were dissolved in 15 ml of ethanol. Then 0.77 g (7.2 mmol) of pyridine-4-carbaldehyde, dissolved in 25 ml of ethanol was added dropwise over the course of 30 minutes. A solution of 1.44 g (7.2 mmol) of copper(II) sulfate in 20 ml of water was then rapidly added dropwise. The mixture was boiled under reflux for 2 hours. The reaction solution was then allowed to cool to 50° C. 2.25 ml of 32% strength hydrochloric acid were then added. A solution of 2.13 g (8.9 mmol) of sodium sulfide hydrate and 25 ml of water was then cautiously added dropwise while hot. The mixture was stirred for 10 minutes. The reaction mixture was then poured into ice-water, and the resulting precipitate was filtered off. The filtrate was made alkaline with aqueous sodium bicarbonate solution and extracted with ethyl acetate. The organic phase was washed with water, dried and concentrated in vacuo. 1.15 g of the product were obtained.

Workup

  1. additionwas added dropwise over the course of 30 minutes
  2. temperatureunder reflux for 2 hours
  3. filtrationthe resulting precipitate was filtered off
  4. extractionextracted with ethyl acetate
  5. washThe organic phase was washed with water
  6. customdried
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-45f3b7630a4d46fe96786ca37e2350c4
Source dataset
uspto-grants-2004_02
Patent number
US06696437B1

Reaction notes

Loading…