4-Fluoro-3-nitrobenzoic acid → 4-fluoro-3-nitro-N-[3-(2-oxo-pyrrolidin-1-yl)-propyl]-benzamide

HRID 710019Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 710019
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].C1C=CC2N([OH:23])N=NC=2C=1.CCN=C=[N:28][CH2:29][CH2:30][CH2:31][N:32]([CH3:34])[CH3:33].Cl.CCN([CH:42]([CH3:44])C)C(C)C>C(Cl)Cl.O>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:28][CH2:29][CH2:30][CH2:31][N:32]2[CH2:33][CH2:44][CH2:42][C:34]2=[O:23])=[O:8])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Komponenten

7

Edukt 4

HCID 679874-Fluoro-3-nitrobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Produkt 1

HCID 712246724-fluoro-3-nitro-N-[3-(2-oxo-pyrrolidin-1-yl)-propyl]-benzamideAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4-fluoro-3-nitro-benzoic acid (5.0 g, 27.02 mmol) in CH2Cl2 (150 mL), HOBt (6.5 g, 48.63 mmol) and EDC.HCl (6.2 g, 40.53 mmol) were added followed by DIPEA (6.12 mL, 35.12 mmol). The reaction was stirred at room temperature for 6 h. Water (50.0 mL) was added and the layers were separated. Organic layer was washed with brind and concentrated to give crude product 4-fluoro-3-nitro-N-[3-(2-oxo-pyrrolidin-1-yl)-propyl]-benzamide (7.5 g, 90%). This was taken to the next step without further purification.

Aufarbeitung

  1. customthe layers were separated
  2. washOrganic layer was washed
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-619b0411ec544e5e9628b1b41a81e9b5
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181226B2

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