Propanal → HCID 21476290, compound

HRID 2293104Notes

Reaction equation

HRID 2293104 reaction equation
[CH:1](=O)[CH2:2][CH3:3].[NH2:5][CH2:6][CH:7]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:16]3[CH2:17][CH2:18][C:19](=[O:22])[NH:20][N:21]=3)[CH:13]=2)[CH2:8]1.[BH4-].[Na+]>CO>[CH2:1]([NH:5][CH2:6][CH:7]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:16]3[CH2:17][CH2:18][C:19](=[O:22])[NH:20][N:21]=3)[CH:13]=2)[CH2:8]1)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 527PropanalHCID 4311764Sodium borohydrideHCID 21476304HCID 21476304, compound

Product 1

HCID 21476290HCID 21476290, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

1.51 g of propanal dissolved in 5 ml of methanol was added dropwise to 6.15 g of 2-aminomethyl-5-[4,5-dihydropyridazin-3(2H)-on-6-yl]indane dissolved in 60 ml of methanol. The mixture was stirred at room temperature for 30 minutes. Then, under ice cooling, 1.03 g of sodium borohydride was added to the mixture. The resulting mixture was stirred at the same temperature for 20 minutes and then stirred at room temperature for 1 hour. After methanol was removed, water was added to the residue, and the residue was extracted with ethyl acetate. After the organic layer was washed with water and dried, the solvent was removed. The residue was purified by silica gel column chromatography (solvent: chloroform-methanol (15:1)) to obtain 5.22 g of 2-(propylaminomethyl)-5-[4,5-dihydropyridazin-3(2H)-on-6-yl]indane.

Workup

  1. stirringThe resulting mixture was stirred at the same temperature for 20 minutes
  2. stirringstirred at room temperature for 1 hour
  3. customAfter methanol was removed
  4. additionwater was added to the residue
  5. extractionthe residue was extracted with ethyl acetate
  6. washAfter the organic layer was washed with water
  7. customdried
  8. customthe solvent was removed
  9. customThe residue was purified by silica gel column chromatography (solvent: chloroform-methanol (15:1))

Sources & evidence

ORD record
ord-9f1206227cd2407f92671b6086945a3b
Source dataset
uspto-grants-1997_11
Patent number
US05686452

Reaction notes

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