(4-Nitrophenyl)acetic acid → 2-(4-Nitrophenyl)acetohydrazide

HRID 1661798

Reaktionsgleichung

Reaktionsgleichung von HRID 1661798
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([OH:13])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(Cl)(=O)C(Cl)=O.CN(C=O)C.[NH2:25][NH2:26]>ClCCl>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([NH:25][NH2:26])=[O:13])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Komponenten

6

Edukt 4

HCID 4661(4-Nitrophenyl)acetic acidHCID 6228DimethylformamideHCID 9321HydrazineHCID 65578Oxalyl chloride

Produkt 1

HCID 2873312-(4-Nitrophenyl)acetohydrazide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 4-nitrophenylacetic acid (2.81 mmol) in dry dichloromethane (10 ML) was treated with a 2N solution of oxalyl chloride (3.0 mL) and DMF (0.02 mL) via syringe, and the reaction stirred at ambient temperature for 1 h. The reaction was concentrated to dryness in vacuo and the crude product was dissolved in dry dichloro-methane (20 mL), treated with anhydrous hydrazine (11.1 mmol) via syringe, and stirred at ambient temperature for 18 h. The resulting suspension was filtered, solids rinsed with dichloromethane, dissolved in MeOH/CH2Cl2, filtered, and filtrate concentrated in vacuo giving the title compound as an orange solid. 1H NMR (DMSO-d6) δ 8.17 (2H, d, J=8.8 Hz,), 7.54 (2H, d, J=8.8 Hz), 3.54 (2H, s).

Aufarbeitung

  1. concentrationThe reaction was concentrated to dryness in vacuo
  2. dissolutionthe crude product was dissolved in dry dichloro-methane (20 mL)
  3. stirringstirred at ambient temperature for 18 h
  4. filtrationThe resulting suspension was filtered
  5. washsolids rinsed with dichloromethane
  6. dissolutiondissolved in MeOH/CH2Cl2
  7. filtrationfiltered
  8. concentrationfiltrate concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f7f7132b2e5348c8a623f92f4956e1f1
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08030305B2

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