Ethanol → HCID 61962718, compound

HRID 1485468Notes

Reaction equation

HRID 1485468 reaction equation
[F:1][C:2]1[C:3]([N+:16]([O-])=O)=[C:4]([NH:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:5]=[CH:6][CH:7]=1.CCO>[Pd].CCOC(C)=O>[NH2:16][C:3]1[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=1[NH:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

5

Reactant 2

HCID 702EthanolHCID 55135599HCID 55135599, compound

Product 1

HCID 61962718HCID 61962718, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A round bottomed flask was charged with palladium on carbon (0.306 g, 0.287 mmol) and a stirbar. Ethyl 3-(3-fluoro-2-nitrophenylamino)propionate (1.473 g, 5.75 mmol) in 1:1 EtOH:EtOAc (40 mL) was added, and the flask was evacuated and purged with hydrogen three times before being stirred at room temperature overnight. The mixture was filtered, concentrated with celite, and purified by silica gel chromatography (eluting with hexanes/ethyl acetate) to yield ethyl 3-(2-amino-3-fluorophenylamino)propanoate as a brown oil (1.074 g, 4.75 mmol, 83%).

Workup

  1. customthe flask was evacuated
  2. custompurged with hydrogen three times
  3. filtrationThe mixture was filtered
  4. concentrationconcentrated with celite
  5. custompurified by silica gel chromatography (eluting with hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-5cf339f9dcd743afaf89cbe1224ed6c1
Source dataset
uspto-grants-2016_08
Patent number
US09422292B2

Reaction notes

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