Hydrazine hydrate (1:1) → 4-(4-Hydroxy-phenyl)-butyric acid hydrazide

HRID 968821

Reaktionsgleichung

Reaktionsgleichung von HRID 968821
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11]([O:13]C)=O)=[CH:4][CH:3]=1.O.[NH2:16][NH2:17]>CO>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11]([NH:16][NH2:17])=[O:13])=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 1409044-(4-Hydroxyphenyl)butanoic acid methyl ester

Produkt 1

HCID 42648864-(4-Hydroxy-phenyl)-butyric acid hydrazideAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of methyl 4-(4-hydroxyphenyl)butyrate (4.93 g, 0.025 mol) and hydrazine hydrate (25.4 g, 0.254 mol) in methanol (64 mL) was heated under reflux for an hour. It was then cooled down to room temperature and stirred overnight. The solvent was evaporated and the residue was partitioned between ethyl acetate (100 mL) and water (100 mL). The organic layer was dried over Na2SO4, filtered and concentrated to dryness to give the titled compound as a white crystal (3.30 g, 67%). 400 MHz 1H NMR (DMSO-d6) δ 9.10 (s, 1H), 8.89 (s, 1H), 6.93 (d, J=8.8 Hz, 2H), 6.63 (d, J=8.8 Hz, 2H), 3.32 (s, 2H), 2.40 (t, J=7.6 Hz, 2H), 1.97 (t, J=7.2 Hz, 2H), 1.71−1.67 (m, 2H); Mass (M−H−)=193.27.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for an hour
  3. customThe solvent was evaporated
  4. customthe residue was partitioned between ethyl acetate (100 mL) and water (100 mL)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-20507ce0f50949749ab2ff787fffc195
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07304062B2

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