Tert-Butylamine → 1-(tert-Butylamino)-3-[2-(6-chloropyridazin-3-yl)phenoxy]propan-2-ol

HRID 1759362Notes

Reaction equation

HRID 1759362 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[O:14][CH2:15][CH:16]2[O:18][CH2:17]2)=[CH:6][CH:7]=1.[C:19]([NH2:23])([CH3:22])([CH3:21])[CH3:20]>CO>[Cl:1][C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[O:14][CH2:15][CH:16]([OH:18])[CH2:17][NH:23][C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 13023013HCID 13023013, compound

Product 1

HCID 30190301-(tert-Butylamino)-3-[2-(6-chloropyridazin-3-yl)phenoxy]propan-2-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3-chloro-6-(2-epoxypropoxyphenyl)pyridazine (0.7 g.), methanol (7 ml.) and t-butylamine (1.7 ml.) was stirred and heated under reflux for 1.25 hours. The mixture was evaporated under reduced pressure at 50° and the residue was recrystallized from toluene to give 3-chloro-6-[2-(3-t-butylamino-2-hydroxypropoxy)phenyl]pyridazine, m.p. 136.5°-137.5°. A sample of this product was treated with hydrochloric acid (1.0 N, 3.62 ml.), the solution was extracted with dichloromethane and the aqueous solution was evaporated under reduced pressure and the residue was recrystallized from ethanol/ether to give the monohydrochloride salt, m.p. 193.5°-194.5°.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1.25 hours
  3. customThe mixture was evaporated under reduced pressure at 50°
  4. customthe residue was recrystallized from toluene

Sources & evidence

ORD record
ord-1cb8d34c4d68468b9ed5b6314c81a835
Source dataset
uspto-grants-1982_07
Patent number
US04340733

Reaction notes

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