Formic Acid → Methyl 5-formamido-2,4-dimethoxybenzoate

HRID 2293548Notes

Reaction equation

HRID 2293548 reaction equation
[C:1](OC(=O)C)(=[O:3])C.C(O)=O.[NH2:11][C:12]1[C:13]([O:24][CH3:25])=[CH:14][C:15]([O:22][CH3:23])=[C:16]([CH:21]=1)[C:17]([O:19][CH3:20])=[O:18]>O1CCCC1>[CH3:23][O:22][C:15]1[CH:14]=[C:13]([O:24][CH3:25])[C:12]([NH:11][CH:1]=[O:3])=[CH:21][C:16]=1[C:17]([O:19][CH3:20])=[O:18]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 16638096Methyl 5-amino-2,4-dimethoxybenzoate

Product 1

HCID 21476992Methyl 5-formamido-2,4-dimethoxybenzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A 1.96 g portion of acetic anhydride was mixed with 0.89 ml of formic acid, followed by stirring at 50° C. for 2 hours. The resulting solution was mixed with 1.5 g of methyl 5-amino-2,4-dimethoxybenzoate dissolved in advance in 3 ml of tetrahydrofuran, followed by 6 hours stirring. After completion of the reaction, the thus precipitated product of interest was collected by filtration, washed with diethyl ether and then dried under a reduced pressure to give 1.62 g of methyl 2,4-dimethoxy-5-formylaminobenzoate.

Workup

  1. waitfollowed by 6 hours
  2. stirringstirring
  3. customAfter completion of the reaction
  4. filtrationthe thus precipitated product of interest was collected by filtration
  5. washwashed with diethyl ether
  6. customdried under a reduced pressure

Sources & evidence

ORD record
ord-8d88c30bdf264bebb0a87b554c11fdc7
Source dataset
uspto-grants-1997_11
Patent number
US05686482

Reaction notes

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