Sodium hydride → HCID 11022760, compound

HRID 849007Notes

Reaction equation

HRID 849007 reaction equation
[OH:1][CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](=[O:13])[N:5]([CH3:14])[N:4]=1.[H-].[Na+].F[C:18]1[CH:25]=[CH:24][C:21]([CH:22]=[O:23])=[CH:20][CH:19]=1>CN(C=O)C>[CH3:14][N:5]1[N:4]=[C:3]([CH2:2][O:1][C:18]2[CH:25]=[CH:24][C:21]([CH:22]=[O:23])=[CH:20][CH:19]=2)[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:13]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 680234-FluorobenzaldehydeHCID 12649914HCID 12649914, compound

Product 1

HCID 11022760HCID 11022760, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

##STR29## To a stirred solution of 4-hydroxymethyl-2-methyl-1(2H)-pthalazinone (350 mg, 1.84 mmol) (prepared according to the procedure described in Chem. Pharm. Bull., 28 (1980) 2763) in dry DMF (30 mL) was added NaH (88 mg, 3.68 mmol) in portions over 30 min at 25-30° C., followed by 4-fluorobenzaldehyde (228 mg, 1.84 mmol) added dropwise, keeping the temperature between 0-15° C. The reaction mixture was stirred at room temperature further for 6 h. Ice (200 g) was added to the reaction mixture and extracted with EtOAc. The EtOAc layer was washed with water, dried over anhydrous Na2SO4 and concentrated to obtain the title compound (300 mg, 50%). mp: 168-170° C.

Workup

  1. additionadded dropwise
  2. custombetween 0-15° C
  3. extractionextracted with EtOAc
  4. washThe EtOAc layer was washed with water
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-27cbf003b4264595b83cba1096c10187
Source dataset
uspto-grants-2000_01
Patent number
US06011036

Reaction notes

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