Sulfuric Acid → HCID 19093694, compound

HRID 487386Notes

Reaction equation

HRID 487386 reaction equation
[C:1]([C:9]1[C:10]([CH3:28])=[N:11][C:12]([CH2:26][CH3:27])=[CH:13][C:14]=1[NH:15]S(C1C=CC(C)=CC=1)(=O)=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O.C(=O)([O-])[O-].[K+].[K+]>>[NH2:15][C:14]1[CH:13]=[C:12]([CH2:26][CH3:27])[N:11]=[C:10]([CH3:28])[C:9]=1[C:1](=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 11430Potassium CarbonateHCID 19093722HCID 19093722, compound

Product 1

HCID 19093694HCID 19093694, compoundYield 70.4%

Conditions

Temperature
55 °C

Procedure

Compound C (1.4 g) was added to concentrated sulphuric acid (6 ml) and the mixture was stirred and heated at 55° C. for 1.5 hours. The reaction mixture was cooled to ambient temperature and poured onto crushed ice. The mixture was then basified by addition of solid potassium carbonate and then extracted with dichloromethane. The combined extracts were dried (MgSO4) and solvent was removed by evaporation to leave a solid. The solid was washed with petroleum ether and collected by filtration to give 4-amino-3-benzoyl-6-ethyl-2-methylpyridine (D) (0.6 g); NMR (d6 -DMSO): 1.19(t, 3H), 1.97(s, 3H), 2.55(q, 2H), 5.85(s, 2H), 6.41(s, 1H), 7.45-7.75(complex m, 5H); mass spectrum (CI, ammonia): 241(M+H)+ ; and which was used without further purification.

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. additionpoured
  3. customonto crushed ice
  4. extractionextracted with dichloromethane
  5. dry with materialThe combined extracts were dried (MgSO4) and solvent
  6. customwas removed by evaporation
  7. customto leave a solid
  8. washThe solid was washed with petroleum ether
  9. filtrationcollected by filtration

Sources & evidence

ORD record
ord-1df6996bd92a4c0ebbc15c7d8522a450
Source dataset
uspto-grants-1994_03
Patent number
US05294620

Reaction notes

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