Hydrochloric Acid → HCID 14442113, compound

HRID 2291552Notes

Reaction equation

HRID 2291552 reaction equation
Cl[C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].[NH2:11][C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=1)[C:15]([OH:17])=[O:16].[C:21](=O)([O-])[O-].[K+].[K+].Cl.[K+].[Br-].CN(C)[CH:32]=[O:33]>CO.[Cu]>[C:15]([C:14]1[CH:13]=[C:12]([NH:11][C:2]2[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=2[C:4]([O:33][CH3:32])=[O:5])[CH:20]=[CH:19][CH:18]=1)([O:17][CH3:21])=[O:16]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 74193-Aminobenzoic AcidHCID 83742-Chlorobenzoic AcidHCID 11430Potassium CarbonateHCID 253877Potassium Bromide

Product 1

HCID 14442113HCID 14442113, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 887MethanolSolvent

Procedure

To a 500 ml round-bottomed flask equipped with condenser and N2 inlet were added 15.7 g (0.10 mol) 2-chlorobenzoic acid, 23.3 g (0.17 mol) 3-aminobenzoic acid, 23.5 g (0.17 mol) potassium carbonate, 50 mg copper powder, and 40 ml dimethylformamide. The mixture was heated to reflux, and three 50 mg portions of methanol-washed copper(I) bromide were added. The reaction was refluxed 3.5 hours, cooled, and poured into 1 l 1N HCl. The mixture was stirred for 10 minutes, filtered, and the filtered solid washed with water, methanol, and ether, and dried to afford a gray solid, mp 277°-279° C., 19 g (73.9%). The acid was taken up in 250 ml methanol, the solution saturated with HCl and refluxed 40 hours, and cooled and evaporated. The residue was chromatographed on silica gel using methylene chloride as eluent to afford 17.46 g (61.3% overall) of a yellow oil. NMR (d, CDCl3): 3.97 (s, 3H), 6.7-8.0 (m, 8H). IR (Cm.-1, KBr): 1730 (C=0).

Workup

  1. customTo a 500 ml round-bottomed flask equipped with condenser and N2 inlet
  2. temperatureThe mixture was heated
  3. temperatureto reflux
  4. washthree 50 mg portions of methanol-washed copper(I) bromide
  5. additionwere added
  6. temperatureThe reaction was refluxed 3.5 hours
  7. temperaturecooled
  8. additionpoured into 1 l 1N HCl
  9. filtrationfiltered
  10. washthe filtered solid washed with water, methanol, and ether
  11. customdried
  12. customto afford a gray solid, mp 277°-279° C., 19 g (73.9%)
  13. temperaturecooled
  14. customevaporated
  15. customThe residue was chromatographed on silica gel
  16. customto afford 17.46 g (61.3% overall) of a yellow oil

Sources & evidence

ORD record
ord-76ad14467f2e4f1c9f2c0083eb54165f
Source dataset
uspto-grants-1989_01
Patent number
US04797403

Reaction notes

Loading…