Benzaldehyde → HCID 12391761, compound

HRID 2042542Notes

Reaction equation

HRID 2042542 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:10][CH2:11][C:12](=[O:15])[NH:13][N:14]=2)=[CH:5][CH:4]=1.[OH-].[K+].CCO.[CH:21](=O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CCO>[CH2:21]([C:11]1[C:12](=[O:15])[NH:13][N:14]=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH:10]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 6891096-(4-Methoxyphenyl)-4,5-dihydropyridazin-3(2H)-oneHCID 21946426Potassium hydroxide ethanol

Product 1

HCID 12391761HCID 12391761, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

6-(4-methoxy-phenyl)-4,5-dihydro-2H-pyridazin-3-one (1.65 g, 7.5 mmol) in 15 mL of EtOH was heated to 80° C. as 20 mL of 4% of KOH/EtOH solution was added dropwise. After 5 min., benzaldehyde (1.0 eq. 0.76 mL) was added and the mixture stirred at 80° C. for 2 h. The reaction was cooled to rt., poured into ice-H2O (75 mL) and the resulting solid was collected and crystallized from EtOH to give 1.67 g (76%) of intermediate 4-benzyl-6-(4-methoxy-phenyl)-2H-pyridazin-3-one: MS m/z 293 (M+H). This intermediate was used to prepare examples 45 and example 46.

Workup

  1. additionwas added dropwise
  2. temperatureThe reaction was cooled to rt
  3. customthe resulting solid was collected
  4. customcrystallized from EtOH

Sources & evidence

ORD record
ord-c14a3cffcd3442c4a3deb0bbcf242167
Source dataset
uspto-grants-2013_11
Patent number
US08586588B2

Reaction notes

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