4-Chloro-1-fluoro-2-nitrobenzene → HCID 22405277, compound

HRID 1500946Notes

Reaction equation

HRID 1500946 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](F)=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.Cl.[NH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].C(N(C(C)C)C(C)C)C>O1CCCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

6

Reactant 3

HCID 676604-Chloro-1-fluoro-2-nitrobenzeneHCID 81531DiisopropylethylamineHCID 458475beta-Alanine, ethyl ester, hydrochloride

Product 1

HCID 22405277HCID 22405277, compoundYield 64.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-chloro-1-fluoro-2-nitrobenzene (10.0 g, 57.0 mmol), ethyl 3-aminopropanoate hydrochloride (8.75 g, 57.0 mmol) and N-ethyl-N-isopropylpropan-2-amine (36.0 g, 0.285 mol) in tetrahydrofuran (150 mL) was stirred at room temperature for 16 hours. The reaction mixture was then diluted with water and then extracted with EtOAc (200 mL×3). The combined organic layers were washed with water (200 mL×3), and then dried over Na2SO4, then filtered and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc:PE=1:2) to afford ethyl 3-[(4-chloro-2-nitrophenyl)amino]propanoate (10.0 g, yield: 64.5%).

Workup

  1. extractionextracted with EtOAc (200 mL×3)
  2. washThe combined organic layers were washed with water (200 mL×3)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (EtOAc:PE=1:2)

Sources & evidence

ORD record
ord-f4b86992d32a4bddba0dd086a13ffa95
Source dataset
uspto-grants-2015_12
Patent number
US09206191B2

Reaction notes

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