Isopropylamine → 6-[3-Allyl-4-(2-hydroxy-3-isopropylaminopropoxy)phenyl]-4,5-dihydro-3(2H)-pyridazinone

HRID 596682Notes

Reaction equation

HRID 596682 reaction equation
[CH2:1]([C:4]1[CH:5]=[C:6]([C:15]2[CH2:16][CH2:17][C:18](=[O:21])[NH:19][N:20]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH:12]1[O:14][CH2:13]1)[CH:2]=[CH2:3].[CH:22]([NH2:25])([CH3:24])[CH3:23]>CO>[CH2:1]([C:4]1[CH:5]=[C:6]([C:15]2[CH2:16][CH2:17][C:18](=[O:21])[NH:19][N:20]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH:12]([OH:14])[CH2:13][NH:25][CH:22]([CH3:24])[CH3:23])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 21450254HCID 21450254, compound

Product 1

HCID 214502186-[3-Allyl-4-(2-hydroxy-3-isopropylaminopropoxy)phenyl]-4,5-dihydro-3(2H)-pyridazinoneYield 119.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred mixture of 6-[3-allyl-4-(2,3-epoxypropoxy)-phenyl]-4,5-dihydro-3(2H)-pyridazinone (46g, 0.16 mole), methanol (500 ml) and isopropylamine (85 ml, 1 mole) was heated under reflux for 60 minutes. Evaporation of the solution under reduced pressure gave an oil (66 g) which was purified on a silica column by elution with mixtures of chloroform and methanol to give 6-[3-allyl-4-(2-hydroxy-3-isopropylaminopropoxy)phenyl]-4,5-dihydro-3(2H)-pyridazinone (45g, 85%, m.p. 94°-96.5° C). The hemisulphate hemihydrate, crystallised from aqueous ethanol, had m.p. 238°-242° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 60 minutes
  3. customEvaporation of the solution under reduced pressure

Sources & evidence

ORD record
ord-4b9bd8a2c951408f9e716341e076c11c
Source dataset
uspto-grants-1977_03
Patent number
US04011321

Reaction notes

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