4-Aminobenzoic Acid → HCID 19351110, compound

HRID 1636376Notes

Reaction equation

HRID 1636376 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Al].N[C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=1.[C:18](=[O:21])([O-])[O-].[Na+].[Na+]>C(#N)C.O1CCOCC1.O.[Cl-].[Na+].O.C1COCC1>[C:3]1(/[CH:4]=[CH:5]/[CH2:6][NH:1][C:18]([C:9]2[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=2)=[O:21])[CH:5]=[CH:4][CH:3]=[CH:2][CH:2]=1

Participants

10

Reactant 4

HCID 9784-Aminobenzoic AcidHCID 1049PyridineHCID 10340Sodium CarbonateHCID 5359268Aluminum

Product 1

HCID 19351110HCID 19351110, compoundYield 18%

Reagents, catalysts & solvents 5

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
20 °C

Procedure

1.75 g (13 mmoles) of trans-cinnamol were dissolved in 130 ml of acetonitrile under argon atmosphere, then 5 g (19 mmoles) of N,N'-disuccinimidyl-carbonate were added heating until complete dissolution, then the mixture was cooled at 20° C. and added with pyridine (0.65 ml, 1 g, 12 mmoles). The reaction mixture was covered with aluminium and stirred at room temperature for 30 hours. The solvent was evaporated off in the cold, the residue was taken up into ethyl acetate and washed repeatedly with 0.1N HCl, finally with water. The solution was dried, then evaporated to dryness in the cold, to give a crude which was dissolved in 26 ml of dioxane and added to a solution of p-aminobenzoic acid (1.79 g, 13 mmoles) in 26 ml of water with 1.38 (13 mmoles) of sodium carbonate. The solution was stirred at room temperature for 60 hours, then added with THF and brine. The organic phase was separated and washed with 0.1N HCl (twice) and again with brine, then dried and !portata a secco stripped. The resulting crude was taken up into isopropyl ether and filtered, thereby obtaining 0.7 g of (E)-4-[(3-phenyl-prop-2-enyl)-carbamoyl]benzoic acid (18% yield); m.p.=176-178° C.

Workup

  1. temperatureheating until complete dissolution
  2. customThe solvent was evaporated off in the cold, the residue
  3. washwashed repeatedly with 0.1N HCl, finally with water
  4. customThe solution was dried
  5. customevaporated to dryness in the cold,
  6. customto give a crude which
  7. stirringThe solution was stirred at room temperature for 60 hours
  8. customThe organic phase was separated
  9. washwashed with 0.1N HCl (twice) and again with brine
  10. customdried
  11. filtrationfiltered

Sources & evidence

ORD record
ord-65a503da2779442ab947964c47d467da
Source dataset
uspto-grants-2000_03
Patent number
US06034096

Reaction notes

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