Water → HCID 13604739, compound

HRID 985940Notes

Reaction equation

HRID 985940 reaction equation
[CH:1]([C:3]1[CH:7]=[CH:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]3[N:19]=[N:18][C:17](=[O:20])[CH2:16][CH:15]3[CH3:21])=[CH:10][CH:9]=2)[CH:4]=1)=[O:2].[BH4-].[Na+].C(Cl)Cl.CO.O>C(O)C.CN(C)C=O>[OH:2][CH2:1][C:3]1[CH:7]=[CH:6][N:5]([C:8]2[CH:9]=[CH:10][C:11]([C:14]3[CH:15]([CH3:21])[CH2:16][C:17](=[O:20])[NH:18][N:19]=3)=[CH:12][CH:13]=2)[CH:4]=1

Participants

7

Reactant 4

HCID 962WaterHCID 4311764Sodium borohydrideHCID 21226129Dichloromethane methanolHCID 86741905HCID 86741905, compound

Product 1

HCID 13604739HCID 13604739, compoundYield 58.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

4.2 g (15 millimoles) of 6-[p-(3-formylpyrrol-1-yl)-phenyl]-5, 6-dihydro-5-methylpyridazin-3-one (Example 1A) were dissolved in 50 ml of ethanol and 20 ml of dimethylformamide (DMF), and 1.15 g (30 millimoles) of sodium borohydride were added. The mixture was stirred for 6 hours at 60° C. (conversion monitored by thin layer chromatography using SiO2 and 9:1 CH2Cl2 /CH3OH), after which 50 ml of water were added, the mixture was extracted with ethyl acetate, the ethyl acetate phase was dried and the solvent was stripped off in a rotary evaporator to give a yellow crystalline solid. Recrystallization from DMF/H2O gave 2.5 g of 6-[p-(3-hydroxymethyl-pyrrol-1-yl)-phenyl]-4, 5-dihydro-5-methylpyridazinone of melting point 184°-186° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialthe ethyl acetate phase was dried
  3. customthe solvent was stripped off in a rotary evaporator
  4. customto give a yellow crystalline solid
  5. customRecrystallization from DMF/H2O

Sources & evidence

ORD record
ord-312bdba6e5a84edbb84ba0627b4b97bf
Source dataset
uspto-grants-1987_12
Patent number
US04710496

Reaction notes

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