Isopropylamine → HCID 21450245, compound

HRID 596677Notes

Reaction equation

HRID 596677 reaction equation
[O:1]1[CH2:22][CH:2]1[CH2:3][O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([C:15]2[CH2:16][CH2:17][C:18](=[O:21])[NH:19][N:20]=2)=[CH:7][CH:6]=1.[CH:23]([NH2:26])([CH3:25])[CH3:24]>CO>[OH:1][CH:2]([CH2:22][NH:26][CH:23]([CH3:25])[CH3:24])[CH2:3][O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([C:15]2[CH2:16][CH2:17][C:18](=[O:21])[NH:19][N:20]=2)=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 214502226-[4-(2,3-epoxypropoxy)-1-naphthyl]-4,5-dihydro-3(2H)-pyridazinone

Product 1

HCID 21450245HCID 21450245, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 6-[4-(2,3-epoxypropoxy)-1-naphthyl]-4,5-dihydro-3(2H)-pyridazinone (10 g, 0.034 mole), methanol (100 ml) and isopropylamine (17.4 ml, 0.2 mole) was heated under reflux for one hour. Evaporation under reduced pressure gave an oil which was purified on a silica column with chloroform-methanol to give 6-[4-(2-hydroxy-3-isopropylaminopropoxy)-1-naphthyl]-4,5-dihydro-3(2H)-pyridazinone (9g, 75%, m.p. 131°-135° C.). The hydrochloride, crystallised from 2-propanol had m.p. 195°-197° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for one hour
  3. customEvaporation under reduced pressure
  4. customgave an oil which
  5. customwas purified on a silica column with chloroform-methanol

Sources & evidence

ORD record
ord-31bb76df3f0145dc91bceccc7520390f
Source dataset
uspto-grants-1977_03
Patent number
US04011321

Reaction notes

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