Hydrochloric Acid → HCID 14442113, compound

HRID 1636888Notes

Reaction equation

HRID 1636888 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-buttomed flask equipped with condenser and N2 inlet are 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 is heated to reflux, and three 50 mg portions of methanol-washed copper #(I) bromide are added. The reaction is refluxed 3.5 hours, cooled, and poured into 1 1 1N HC1. The mixture is 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 is taken up in 250 ml methanol, the solution is saturated with HCl and refluxed 40 hours, and cooled and evaporated. The residue is chromatographed on silica gel using methylene chloride as eluent to afford 17.46 g (61.3% overall) of a yellow oil. NMR (d, CDC13): 3.97 (s, 3H), 6.7-8.0 (m, 8H). IR (Cm.-1, KBr): 1730 (C=O).

Workup

  1. customTo a 500 ml round-buttomed flask equipped with condenser and N2 inlet
  2. temperatureThe mixture is heated
  3. temperatureto reflux
  4. washthree 50 mg portions of methanol-washed copper #(I) bromide
  5. additionare added
  6. temperatureThe reaction is refluxed 3.5 hours
  7. temperaturecooled
  8. additionpoured into 1 1 1N HC1
  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. temperaturerefluxed 40 hours
  14. temperaturecooled
  15. customevaporated
  16. customThe residue is chromatographed on silica gel
  17. customto afford 17.46 g (61.3% overall) of a yellow oil

Sources & evidence

ORD record
ord-728f61f255b7433da116720dec5be10b
Source dataset
uspto-grants-2000_03
Patent number
US06037345

Reaction notes

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