Formic Acid → Methyl 4-formamido-3-methoxybenzoate

HRID 2076265Notes

Reaction equation

HRID 2076265 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 liquid was stirred at room temperature for 40 minutes. A THF (600 mL) solution of methyl 4-amino-3-methoxybenzoate (134 g) was added dropwise to the reaction liquid at room temperature, and the resultant reaction liquid was stirred for one hour. To the reaction liquid was added 3.8 L of ice water, and the precipitated solid was collected by filtration and further washed with water (2 L). The resultant solid was dried overnight at 50° C. to provide 111 g of the title compound. The physical property values thereof agreed with reported values (CAS#700834-18-0).

Workup

  1. customthe reaction liquid
  2. customthe resultant reaction liquid
  3. stirringwas stirred for one hour
  4. customTo the reaction liquid
  5. filtrationthe precipitated solid was collected by filtration
  6. washfurther washed with water (2 L)
  7. customThe resultant solid was dried overnight at 50° C.

Sources & evidence

ORD record
ord-7efef5847fe142f0b8e29ff78f4903b7
Source dataset
uspto-grants-2011_04
Patent number
US07923563B2

Reaction notes

Loading…