Water → 4-[2-[4-Methyl-1-oxo-1,2-dihydro-phthalazin-2-yl]ethoxy]benzaldehyde

HRID 849008Notes

Reaction equation

HRID 849008 reaction equation
C([O-])([O-])=O.[K+].[K+].[CH3:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11](=[O:18])[NH:10][N:9]=1.Br[CH2:20][CH2:21][O:22][C:23]1[CH:30]=[CH:29][C:26]([CH:27]=[O:28])=[CH:25][CH:24]=1.O>CN(C=O)C>[CH3:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11](=[O:18])[N:10]([CH2:20][CH2:21][O:22][C:23]2[CH:30]=[CH:29][C:26]([CH:27]=[O:28])=[CH:25][CH:24]=2)[N:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 211031-Hydroxy-4-methylphthalazineHCID 2627064-(2-Bromoethoxy)Benzaldehyde

Product 1

HCID 118337894-[2-[4-Methyl-1-oxo-1,2-dihydro-phthalazin-2-yl]ethoxy]benzaldehydeYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
25 °C

Procedure

##STR30## To a stirred suspension of K2CO3 (11.3 g, 82.5 mmol) in dry DMF (50 mL) at 25-30° C. was added a solution of 4-methyl-1(2H)-phthalazinone (6.6 g, 41.25 mmol) (Ref: Chemistry of Heterocyclic Compounds; Condensed Pyridazines including Cinnolines and Phthalazines, edited by R. N. Castle; John Wiley and Sons, 27, (1973) 375-441) in dry DMF (100 mL). The reaction mixture was stirred for 30 min at 25° C. and 4-(2-bromoethoxy)benzaldehyde (9.4 g, 41.25 mmol) was added. The reaction mixture was immersed in a pre-heated oil bath at 70° C. and stirred at 65-70° C. for 24 h. The reaction mixture was cooled to room temperature and water (50 mL) was added. The reaction mixture was extracted with EtOAc (3×50 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and concentrated. The crude compound was recrystallised from methanol to obtain the title compound (9.7 g, 77%). mp: 90° C.

Workup

  1. customThe reaction mixture was immersed in a pre-heated oil bath at 70° C.
  2. stirringstirred at 65-70° C. for 24 h
  3. temperatureThe reaction mixture was cooled to room temperature
  4. extractionThe reaction mixture was extracted with EtOAc (3×50 mL)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated
  8. customThe crude compound was recrystallised from methanol

Sources & evidence

ORD record
ord-b407195ea4ad4857a8a14b09712d0be5
Source dataset
uspto-grants-2000_01
Patent number
US06011036

Reaction notes

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