Acetic Acid → HCID 13604742, compound

HRID 985941Notes

Reaction equation

HRID 985941 reaction equation
[CH:1]([C:3]1[CH:7]=[CH:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[CH:15]([CH3:21])[CH2:16][C:17](=[O:20])[NH:18][N:19]=3)=[CH:10][CH:9]=2)[CH:4]=1)=O.[CH3:22][NH:23][CH3:24].C(O)(=O)C.C([BH3-])#N.[Na+].[OH-].[Na+]>CO.O.C(OCC)(=O)C.C(O)(=O)C.O>[CH3:22][N:23]([CH2:1][C:3]1[CH:7]=[CH:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[CH:15]([CH3:21])[CH2:16][C:17](=[O:20])[NH:18][N:19]=3)=[CH:10][CH:9]=2)[CH:4]=1)[CH3:24]

Participants

9

Reactant 5

HCID 176Acetic AcidHCID 674DimethylamineHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 13604735HCID 13604735, compound

Product 1

HCID 13604742HCID 13604742, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 86628739HCID 86628739, compoundSolvent

Procedure

4.2 g (15 millimoles) of 6-[p-(3-formylpyrrol-1-yl)-phenyl]4, 5-dihydro-5-methylpyridazin-3-one (compound from Example 1A) in 30 ml of methanol were stirred with 3.36 g (30 millimoles) of 40% strength aqueous dimethylamine solution, 1.8 g (30 millimoles) of acetic acid and 0.75 g (12 millimoles) of sodium cyanoborohydride for 5 hours at room temperature (conversion monitored by thin layer chromatography using SiO2 and 5:2:2 ethyl acetate/acetic acid/water). 50 ml of H2O were added, the mixture was rendered alkaline with 2N NaOH and extracted with ethyl acetate, the organic phase was washed with water, dried with Na2SO4 and purified over a silica gel column using a 4:1 methylene chloride/methanol mixture, and the crystalline residue from the product-containing fractions was recrystallized from ethyl acetate/petroleum ether. 1.4 g of 6-[p-(3-dimethylaminomethylpyrrol-1-yl)-phenyl]-4, 5-dihydro-5-methylpyridazin-3-one of melting point 167°-168° C. were obtained.

Workup

  1. extractionextracted with ethyl acetate
  2. washthe organic phase was washed with water
  3. dry with materialdried with Na2SO4
  4. custompurified over a silica gel column
  5. customthe crystalline residue from the product-containing fractions was recrystallized from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-93bd8ca7de2f428e9564a42b092cc1f5
Source dataset
uspto-grants-1987_12
Patent number
US04710496

Reaction notes

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