Ethyl 2-aminobenzoate → HCID 178517962, compound

HRID 514837Notes

Reaction equation

HRID 514837 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4](OCC)=[O:5].C(O)(=O)C.[CH:17](N)=[NH:18]>COC(O)C>[N:1]1[C:2]2[C:3](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:4]([OH:5])=[N:18][CH:17]=1

Participants

4

Reactant 2

HCID 6877Ethyl 2-aminobenzoateHCID 160693Formamidine acetate2×

Product 1

HCID 178517962HCID 178517962, compoundYield 110.4%

Reagents, catalysts & solvents 1

HCID 30156371-MethoxyethanolSolvent

Procedure

A solution of ethyl 2-aminobenzoate (5.0 g, 30 mmol) in methoxyethanol (20 mL) was treated with formamidine acetate (8 g, 77 mmol) under reflux for 17 h. A second portion of formamidine acetate (8 g, 77 mmol) was then added, and the reflux was continued for 7 more hours. The mixture was cooled, and the solvent was removed under vacuum. The residue was taken in saturated NaHCO3 and extracted with ethyl acetate. The organic layers were combined, washed with saturated NaHCO3, and dried with magnesium sulfate, and the solvent was removed under vacuum to give the desired compound (4.84 g, 91%), which was used for the next step without further purification. LC-MS: m/z 147.7 (M+H)+

Workup

  1. temperatureunder reflux for 17 h
  2. temperatureThe mixture was cooled
  3. customthe solvent was removed under vacuum
  4. extractionextracted with ethyl acetate
  5. washwashed with saturated NaHCO3
  6. dry with materialdried with magnesium sulfate
  7. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-6739552fe2fd49f2b3ab0c2a9ba503df
Source dataset
uspto-grants-2015_08
Patent number
US09108921B2

Reaction notes

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