Formic Acid → 3-(Formylamino)phenylacetic acid ethyl ester

HRID 1760019Notes

Reaction equation

HRID 1760019 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH2:12])[CH:7]=1)[CH3:2].[CH:14](O)=[O:15]>C(OC(C)C)(C)C>[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:12][CH:14]=[O:15])[CH:7]=1)[CH3:2]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 13042040Ethyl 2-(3-aminophenyl)acetate

Product 1

HCID 542316283-(Formylamino)phenylacetic acid ethyl esterYield 89%

Reagents, catalysts & solvents 1

HCID 7914Diisopropyl EtherSolvent

Procedure

A solution of 3-aminophenylacetic acid ethyl ester (3.0 g; 0.017 mol; from Example T(i) above), and formic acid (1.5 g; 0.034 mol) in diisopropylether (150 mL) was refluxed with a Dean-Stark trap overnight. The solution was concentrated to dryness, dissolved in ether and washed with diluted HCl to remove remaining starting material. Drying (N2SO4) and concentration yielded the sub-title compound (3.1 g; 89%).

Workup

  1. customwas refluxed with a Dean-Stark trap overnight
  2. concentrationThe solution was concentrated to dryness
  3. dissolutiondissolved in ether
  4. washwashed with diluted HCl
  5. customto remove
  6. customDrying
  7. concentration(N2SO4) and concentration

Sources & evidence

ORD record
ord-76e5a622d915432790927b7a425f0871
Source dataset
uspto-grants-2005_01
Patent number
US06838478B2

Reaction notes

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