Potassium Carbonate → HCID 55135599, compound

HRID 1485467Notes

Reaction equation

HRID 1485467 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[F:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13](F)[C:12]=1[N+:18]([O-:20])=[O:19].C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[F:10][C:11]1[C:12]([N+:18]([O-:20])=[O:19])=[C:13]([NH:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 879221,3-Difluoro-2-nitrobenzeneHCID 458475beta-Alanine, ethyl ester, hydrochloride

Product 1

HCID 55135599HCID 55135599, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

A round bottomed flask was charged with ethyl 3-aminopropanoate hydrochloride (1 g, 6.51 mmol), 1,3-difluoro-2-nitrobenzene (1.036 g, 6.51 mmol), potassium carbonate (2.70 g, 19.53 mmol), and a stirbar. THF (35 mL, 0.2 M) was added, and the mixture was stirred at 100° C. overnight. The mixture was concentrated with celite and purified by silica gel chromatography (eluting with hexanes/ethyl acetate) to yield ethyl 3-(3-fluoro-2-nitrophenylamino)propionate as a yellow amorphous solid (1.473 g, 5.75 mmol, 88%).

Workup

  1. concentrationThe mixture was concentrated with celite
  2. custompurified by silica gel chromatography (eluting with hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-34c3bcfa3fa640ec918c26bda1914c03
Source dataset
uspto-grants-2016_08
Patent number
US09422292B2

Reaction notes

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