Phenol → HCID 21450255, compound

HRID 596675Notes

Reaction equation

HRID 596675 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 hydrochloric 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-8d5c143b917f44faab360db0bfab9d58
Source dataset
uspto-grants-1977_03
Patent number
US04011321

Reaction notes

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