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

HRID 339710

Reaction equation

HRID 339710 reaction equation
[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

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 5984154-Benzylpyridazine

Product 1

HCID 12486783Phenyl(pyridazin-4-yl)methanone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
100 °C

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-7d2ea79406194ab58aad7f311b3f3114
Source dataset
uspto-grants-2014_11
Patent number
US08895556B2

Linked notes

Loading…