Formic Acid → HCID 20116475, compound

HRID 1910768Notes

Reaction equation

HRID 1910768 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH:15](O)=O>C=O>[CH3:15][N:10]([CH2:11][C:12]([OH:14])=[O:13])[C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 12095Glycine, N-(4-nitrophenyl)-

Product 1

HCID 20116475HCID 20116475, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 712FormaldehydeSolvent

Procedure

A solution of (4-nitro-phenylamino)-acetic acid (1.3 g, 6.6 mmol) in formic acid (5 mL) and formaldehyde (5 mL) was heated at reflux overnight. The mixture was concentrated in vacuo and 1N hydrochloric acid added to the residue giving a pH ˜3. The mixture was extracted with ethyl acetate then the organic phase was washed with water and brine. Concentration in vacuo afforded [methyl-(4-nitro-phenyl)-amino]-acetic acid (1.2 g, 86%) as a yellow solid.

Workup

  1. temperatureat reflux overnight
  2. concentrationThe mixture was concentrated in vacuo and 1N hydrochloric acid
  3. additionadded to the residue
  4. customgiving a pH ˜3
  5. extractionThe mixture was extracted with ethyl acetate
  6. washthe organic phase was washed with water and brine
  7. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-62628ced33c44bd5aa2bf325b5abea16
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

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