Phenol → HCID 21450255, compound

HRID 1579265Notes

Reaction equation

HRID 1579265 reaction equation
[O:1]1[CH2:19][CH:2]1[CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH2:12][CH2:13][C:14](=[O:18])[N:15]([CH3:17])[N:16]=1.C1(O)C=CC=CC=1.[CH:27]([NH2:30])([CH3:29])[CH3:28]>CO>[OH:1][CH:2]([CH2:19][NH:30][CH:27]([CH3:29])[CH3:28])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH2:12][CH2:13][C:14](=[O:18])[N:15]([CH3:17])[N:16]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 6363IsopropylamineHCID 21450246HCID 21450246, compound

Product 1

HCID 21450255HCID 21450255, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 6-[2-(2,3-epoxypropoxy)phenyl]-2-methyl-4,5-dihydro-3(2H)-pyridazinone (1.05 g, 0.004 mole; prepared from the corresponding phenol by the method of Example 1(b)(i), methanol (15 ml) and isopropylamine (2.1 ml, 0.024 mole) was heated under reflux for 90 minutes. The solution was evaporated under reduced pressure to give a viscous oil (1.43 g.), which was purified on a silica column by elution with a mixture of chloroform and methanol to give 6-[2-(2-hydroxy-3-isopropylaminopropoxy)phenyl]-2-methyl-4,5-dihydro-3(2H)-pyridazinone (0.97 g, 75%, m.p. 82°-84°C). The hydrochloride crystallised from 2-propanol, had m.p. 170°-171°C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 90 minutes
  3. customThe solution was evaporated under reduced pressure
  4. customto give a viscous oil (1.43 g.), which
  5. customwas purified on a silica column by elution with a mixture of chloroform and methanol

Sources & evidence

ORD record
ord-14672aa293a745d8af94433f141556be
Source dataset
uspto-grants-1976_01
Patent number
US03931177

Reaction notes

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