Formic Acid → (Formylanilino)acetic acid

HRID 2292838Notes

Reaction equation

HRID 2292838 reaction equation
[C:1]1([NH:7][CH2:8][C:9]([OH:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:12](O)=[O:13].C(OC(=O)C)(=O)C>>[CH:12]([N:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:8][C:9]([OH:11])=[O:10])=[O:13]

Participants

4

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 66025N-Phenylglycine

Product 1

HCID 7099130(Formylanilino)acetic acidYield 3,503.5%

Procedure

7.56 g (50 mmole) of N-phenyl glycine and 54.87 g (1.19 mmole) of formic acid were transferred into a reaction vessel and 16.23 g (159 mol) of acetic anhydride was added dropwise over about 10 minutes while cooling and stirring. The reaction mixture was stirred for one hour at 0° C. and for two hours at room temperature. The resulting reaction mixture was concentrated under vacuum to obtain crude crystals. The crystals were recrystallized from ethanol-isopropyl ether to obtain 7.47 g of the title compound (yield 83.4%).

Workup

  1. temperaturewhile cooling
  2. stirringThe reaction mixture was stirred for one hour at 0° C. and for two hours at room temperature
  3. customThe resulting reaction mixture
  4. concentrationwas concentrated under vacuum
  5. customto obtain crude crystals
  6. customThe crystals were recrystallized from ethanol-isopropyl ether

Sources & evidence

ORD record
ord-950bec4dfffc479ea3330b073752ee64
Source dataset
uspto-grants-1997_11
Patent number
US05684161

Reaction notes

Loading…