HCID 57585867, compound → HCID 57585829, compound

HRID 547619Notes

Reaction equation

HRID 547619 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][CH:12]=[O:13])=[C:7]([N+:14]([O-])=O)[CH:6]=1)(=[O:3])[CH3:2]>C(OCC)(=O)C.[Pd]>[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][CH:12]=[O:13])=[C:7]([NH2:14])[CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 57585867HCID 57585867, compound

Product 1

HCID 57585829HCID 57585829, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

4-(Formylamino)-3-nitrophenyl acetate (13.5 g, 60.3 mmol, split into 1 g, 5 g, and 7.5 g batches) was dissolved in a minimal amount of ethyl acetate. The solution was hydrogenated over 10% Pd on carbon (wet, degussa type) on a Parr hydrogenator at 40 PSI of H2 for 1 hour. The catalyst was removed by filtering the reaction through Celite. The filtrate was concentrated to give 10.3 g of 3-amino-4-(formylamino)phenyl acetate. (M+1) 195.1, 1.31 min (LC/MS method A)

Workup

  1. customThe catalyst was removed
  2. filtrationby filtering
  3. customthe reaction through Celite
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-7e758ba1c7464866b7982efe4fcc06d7
Source dataset
uspto-grants-2011_05
Patent number
US07939528B2

Reaction notes

Loading…