Ici 109,081 → HCID 13604735, compound

HRID 985939Notes

Reaction equation

HRID 985939 reaction equation
C[O:2][CH:3]1[CH:7]([CH:8]=O)[CH2:6][CH:5](OC)O1.[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:20]([CH3:26])[CH2:21][C:22](=[O:25])[NH:23][N:24]=2)=[CH:15][CH:14]=1.C([O-])(O)=O.[Na+]>C(O)(=O)C>[CH:3]([C:7]1[CH:6]=[CH:5][N:12]([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:20]([CH3:26])[CH2:21][C:22](=[O:25])[NH:23][N:24]=3)=[CH:15][CH:14]=2)[CH:8]=1)=[O:2]

Participants

5

Reactant 3

HCID 161928Ici 109,081HCID 516892Sodium BicarbonateHCID 567310Tetrahydro-2,5-dimethoxyfuran-3-carbaldehyde

Product 1

HCID 13604735HCID 13604735, compoundYield 78.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of 33.6 g (210 millimoles) of 2,5-dimethoxytetrahydrofuran-3-carbaldehyde in 200 ml of glacial acetic acid was added dropwise to 40.6 g (200 millimoles) of 6-(4-aminophenyl)-4,5-dihydro-5-methylpyridazinone in 400 ml of glacial acetic acid at 80° C. After 2 hours, the reaction mixture was poured into saturated NaHCO3 solution and extracted with CH2Cl2. The extract was washed with water and saturated NaCl solution and dried over Na2SO4, the solvent was stripped off in a rotary evaporator, and the residue was then recrystallized from dimethylformamide (DMF)/water. 44.2 g of 6-[p-(3-formylpyrrol-1-yl)-phenyl]-4,5-dihydro-5-methylpyridazinone of melting point 191°-192° C. were obtained.

Workup

  1. extractionextracted with CH2Cl2
  2. washThe extract was washed with water and saturated NaCl solution
  3. dry with materialdried over Na2SO4
  4. customthe solvent was stripped off in a rotary evaporator
  5. customthe residue was then recrystallized from dimethylformamide (DMF)/water

Sources & evidence

ORD record
ord-e694c44cf08940e0be1a9872c7d7659e
Source dataset
uspto-grants-1987_12
Patent number
US04710496

Reaction notes

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