Formic Acid → Methyl 4-formamido-3-methoxybenzoate

HRID 71135

Reaction equation

HRID 71135 reaction equation
[CH:1](O)=[O:2].C(OC(=O)C)(=O)C.[NH2:11][C:12]1[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][C:13]=1[O:22][CH3:23]>C1COCC1>[CH:1]([NH:11][C:12]1[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][C:13]=1[O:22][CH3:23])=[O:2]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 602411Methyl 4-amino-3-methoxybenzoate

Product 1

HCID 23085082Methyl 4-formamido-3-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To formic acid (75 mL) was added dropwise acetic anhydride (50 mL) at room temperature, and the mixture was stirred at room temperature for 40 min. A mixture of methyl 4-amino-3-methoxybenzoate (25 g) in THF (100 mL) was added dropwise to the reaction mixture, and the mixture was stirred at room temperature for 1 hr. Ice water (700 mL) was added to the reaction mixture, and the precipitated solid was collected by filtration. The solid was washed with water (400 mL) to give the title compound (25.8 g).

Workup

  1. additionwas added dropwise to the reaction mixture
  2. stirringthe mixture was stirred at room temperature for 1 hr
  3. filtrationthe precipitated solid was collected by filtration
  4. washThe solid was washed with water (400 mL)

Sources & evidence

ORD record
ord-da5866695f654abbb84dcf84c965f3f0
Source dataset
uspto-grants-2014_09
Patent number
US08822699B2

Linked notes

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