Ethyl 2-aminobenzoate → HCID 898498, compound

HRID 1084819Notes

Reaction equation

HRID 1084819 reaction equation
[I-].ClC1C=CC=C[N+]=1C.[S:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[CH:15]=[CH:16][C:17]([OH:19])=O.C(N(CC)CC)C.[NH2:27][C:28]1[CH:38]=[CH:37][CH:36]=[CH:35][C:29]=1[C:30]([O:32][CH2:33][CH3:34])=[O:31]>C(Cl)Cl>[S:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[CH:15]=[CH:16][C:17]([NH:27][C:28]1[CH:38]=[CH:37][CH:36]=[CH:35][C:29]=1[C:30]([O:32][CH2:33][CH3:34])=[O:31])=[O:19]

Participants

6

Reactant 4

HCID 6877Ethyl 2-aminobenzoateHCID 8471TriethylamineHCID 928683-Thiophen-2-ylprop-2-enoic acidHCID 1670692-Chloro-1-methylpyridinium iodide

Product 1

HCID 898498HCID 898498, compoundYield 45.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Under nitrogen stream, 2-chloro-1-methylpyridinium iodide (966 mg, 3.89 mmol) was suspended in dry methylene chloride (5 ml). To the suspension, a solution of 3-(2-thienyl)acrylic acid (500 mg, 3.24 mmol), triethylamine (1.08 ml, 7.78 mmol), and ethyl 2-aminobenzoate (0.48 ml, 3.24 mmol) in dry methylene chloride (5 ml) was added dropwise. After the addition, the mixture was heated under reflux for 39 hours. Then, the reaction mixture was diluted with methylene chloride, washed with 10% aqueous HCl, saturated aqueous sodium chloride, 1N-aqueous NaOH, and saturated aqueous sodium chloride successively, and dried. Removal of solvent gave a yellow solid, which was washed with n-hexane to give pale yellow solids of the title compound (442 mg, yield, 45%). m.p., 126°-127° C. (recrystallized from methanol)

Workup

  1. additionAfter the addition
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 39 hours
  4. washwashed with 10% aqueous HCl, saturated aqueous sodium chloride, 1N-aqueous NaOH, and saturated aqueous sodium chloride successively
  5. customdried
  6. customRemoval of solvent
  7. customgave a yellow solid, which
  8. washwas washed with n-hexane

Sources & evidence

ORD record
ord-f36049eb20524f8bafa9d902836017b1
Source dataset
uspto-grants-1991_04
Patent number
US05006548

Reaction notes

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