3-Nitroaniline → 3-chloro-N-(3-nitrophenyl)propanamide

HRID 716854Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 716854
[N+:1]([C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7])([O-:3])=[O:2].[Cl:11][CH2:12][CH2:13][C:14](Cl)=[O:15]>C1COCC1>[Cl:11][CH2:12][CH2:13][C:14]([NH:7][C:6]1[CH:8]=[CH:9][CH:10]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)=[O:15]

Komponenten

4

Edukt 2

HCID 74233-NitroanilineHCID 693643-Chloropropionyl chloride

Produkt 1

HCID 34652363-chloro-N-(3-nitrophenyl)propanamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a stirred solution of 3-nitroaniline (37a, 6.9 g, 50 mmol) in THF (50 mL) was added dropwise 3-chloropropionyl chloride (10 mL, 100 mmol) over 30 min under argon atmosphere. The reaction was stirred at 50° C. for 10 h. After cooling, the reaction mixture was evaporated to dryness under vacuo and the residue was neutralized with saturated aqueous solution of NaHCO3 and the solid product was collected by filtration, washed with water followed by hexane, and dried to afford 3-chloro-N-(3-nitrophenyl)propanamide, 10.61 g (92%), mp 86-88° C. (Lit. 100-102° C.57). 1H NMR (DMSO-d6) δ: 2.87-2.90 (2H, t, J=9.9 Hz, CH2), 3.90-3.92 (2H, t, J=9.9 Hz, CH2), 7.61-7.64 (1H, t, J=6.6 and 6.6 Hz, Ar—H), 7.90-7.94 (2H, m, Ar—H), 8.65-8.66 (1H, t, J=3.4 and 1.7 Hz, Ar—H), 10.59 (1H, brs, NH).

Aufarbeitung

  1. temperatureAfter cooling
  2. customthe reaction mixture was evaporated to dryness under vacuo
  3. filtrationthe solid product was collected by filtration
  4. washwashed with water
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-62019b26578c45fa93f418931b53bffc
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09193687B2

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