Acetic Acid → Methyl 4-formamido-3-methoxybenzoate

HRID 2247451Notes

Reaction equation

HRID 2247451 reaction equation
[C:1](O)(=[O:3])C.C(O)=O.C1COCC1.[CH3:13][O:14][C:15](=[O:25])[C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[C:18]([O:23][CH3:24])[CH:17]=1>O>[CH3:13][O:14][C:15](=[O:25])[C:16]1[CH:21]=[CH:20][C:19]([NH:22][CH:1]=[O:3])=[C:18]([O:23][CH3:24])[CH:17]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 284Formic AcidHCID 8028TetrahydrofuranHCID 602411Methyl 4-amino-3-methoxybenzoate

Product 1

HCID 23085082Methyl 4-formamido-3-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Anhydrous acetic acid (268 mL) was added dropwise to formic acid (401 mL) at room temperature, and the reaction solution was agitated for 40 minutes at room temperature. To this reaction solution, a THF (600 mL) solution of 4-amino-3-methoxybenzoic acid methyl ester (134 g) was added dropwise at room temperature, and the reaction solution was agitated for 1 hour. 3.8 L of iced water was added to the reaction solution, and the deposited solids were separated by filtering, and further washed with water (2 L). 111 g of the title compound was obtained by drying the obtained solid at 50° C. overnight. The physical properties was in agreement with the reported values (CAS#700834-18-0).

Workup

  1. stirringthe reaction solution was agitated for 1 hour
  2. customthe deposited solids were separated
  3. filtrationby filtering
  4. washfurther washed with water (2 L)

Sources & evidence

ORD record
ord-e60c76f9c5314a90bee689036ac21a66
Source dataset
uspto-grants-2010_03
Patent number
US07687640B2

Reaction notes

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