Sodium Hydroxide → Phenyl(pyridazin-4-yl)methanone

HRID 1258114

Reaktionsgleichung

Reaktionsgleichung von HRID 1258114
[CH2:1]([C:8]1[CH:13]=[CH:12][N:11]=[N:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:14].[Na+]>C(O)(=O)C>[C:2]1([C:1]([C:8]2[CH:13]=[CH:12][N:11]=[N:10][CH:9]=2)=[O:14])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 5984154-Benzylpyridazine

Produkt 1

HCID 12486783Phenyl(pyridazin-4-yl)methanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel2×

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a 100° C. suspension of SeO2 (4.75 g, 0.043 mole) in acetic acid (216 mL) was added dropwise to a solution of 4-benzylpyridazine (11; 7.6 g, 0.044.6 mole) in acetic acid (216 mL). The mixture was heated for 1 hour at 100° C. The reaction mixture was cooled to room temperature and was neutralized to a pH ˜6-7 with 50% NaOH. The neutralized mixture was extracted twice with CH2Cl2. The combined extracts were dried over MgSO4 and were evaporated to dryness. The crude product was purified by crystallization in refluxing isopropyl alcohol (10 vol). The yield of phenylpyridazin-4-yl-methanone (12) obtained was 5.8 g or 66%. MS (ESI+): [M+H]+=185.33; 1H NMR (300 MHz, CDCl3), δ ppm: 7.5-7.60(m, 2H), 7.64-7.83 (m, 4H), 9.42-9.51 (m, 2H).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionThe neutralized mixture was extracted twice with CH2Cl2
  3. dry with materialThe combined extracts were dried over MgSO4
  4. customwere evaporated to dryness
  5. customThe crude product was purified by crystallization
  6. temperaturein refluxing isopropyl alcohol (10 vol)

Quellen und Nachweise

ORD-Eintrag
ord-7f44fb6ed6db45e5b3072c5498dc04b4
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08466151B2

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