Methanol → Hydrochloric Acid

HRID 596688Notes

Reaction equation

HRID 596688 reaction equation
[O:1]1[CH2:21][CH:2]1[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH2:12][CH2:13][C:14](=[O:17])[NH:15][N:16]=2)=[CH:7][C:6]=1[N+:18]([O-:20])=[O:19].[Cl:22]CC(O)COC1C=C[C:30]([C:33]2[CH2:34]CC(=O)N[N:38]=2)=CC=1[N+]([O-])=O.CO.C(N)(C)C>C(Cl)(Cl)Cl.CO>[OH:1][CH:2]([CH2:21][NH:38][CH:33]([CH3:34])[CH3:30])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH2:12][CH2:13][C:14](=[O:17])[NH:15][N:16]=2)=[CH:7][C:6]=1[N+:18]([O-:20])=[O:19].[ClH:22]

Participants

7

Reactant 4

HCID 887MethanolHCID 6363IsopropylamineHCID 21450249HCID 21450249, compoundHCID 21450271HCID 21450271, compound

Product 2

HCID 313Hydrochloric AcidHCID 21450216HCID 21450216, compound

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

A mixture of 6-[4-(2,3-epoxypropoxy)-3-nitrophenyl]-4,5-dihydro-3(2H)-pyridazinone and 6-[4-(3-chloro-2-hydroxypropoxy)-3-nitrophenyl]-4,5-dihydro-3(2H)-pyridazinone (0.9g) was stirred with methanol (9 ml) and isopropylamine (1.6 ml) and heated under reflux for 60 minutes. Evaporation under reduced pressure gave a glassy solid, 0.96g, from which 6-[4-(2-hydroxy-3-isopropylaminopropoxy)-3-nitrophenyl]-4,5-dihydro-3(2H)-pyridazinone was isolated as its hydrochloride (m.p. 210°-215° C) by column chromatography (silica, chloroform-methanol mixtures).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 60 minutes
  3. customEvaporation under reduced pressure
  4. customgave a glassy solid, 0.96g

Sources & evidence

ORD record
ord-83ca71f66b144ce8858da6fbbca756b9
Source dataset
uspto-grants-1977_03
Patent number
US04011321

Reaction notes

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