Formic Acid → Methyl 4-formamido-3-methoxybenzoate

HRID 553845Notes

Reaction equation

HRID 553845 reaction equation
[C:1](OC(=O)C)(=[O:3])C.C(O)=O.[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:3]

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

Acetic anhydride (268 mL) was added dropwise to formic acid (401 mL) at room temperature, and the reaction solution was stirred at room temperature for 40 minutes. A solution of methyl 4-amino-3-methoxybenzoate (134 g) in THF (600 mL) was added dropwise to the reaction solution at room temperature, and the reaction solution was stirred for one hour. 3.8 L of ice water was added to the reaction solution, and the precipitated solid was filtered and further washed with water (2 L). The resulting solid was dried at 50° C. overnight to obtain 111 g of the title compound. The property values corresponded to the reported values (CAS #700834-18-0).

Workup

  1. stirringthe reaction solution was stirred for one hour
  2. filtrationthe precipitated solid was filtered
  3. washfurther washed with water (2 L)
  4. customThe resulting solid was dried at 50° C. overnight

Sources & evidence

ORD record
ord-8042fa55e9e34e0f8f1f3c4d0e676151
Source dataset
uspto-grants-2011_11
Patent number
US08048878B2

Reaction notes

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