2-Aminopropanol → 2-[[6-[3-(Trifluoromethyl)phenyl]-3-pyridazinyl]amino]-1-propanol

HRID 1589460Notes

Reaction equation

HRID 1589460 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)=[CH:6][CH:7]=1.[NH2:18][CH:19]([CH3:22])[CH2:20][OH:21]>O>[F:15][C:14]([F:17])([F:16])[C:10]1[CH:9]=[C:8]([C:5]2[N:4]=[N:3][C:2]([NH:18][CH:19]([CH3:22])[CH2:20][OH:21])=[CH:7][CH:6]=2)[CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 51262-AminopropanolHCID 124495523-Chloro-6-[3-(trifluoromethyl)phenyl]pyridazine

Product 1

HCID 135653562-[[6-[3-(Trifluoromethyl)phenyl]-3-pyridazinyl]amino]-1-propanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 0.5 g of 3-chloro-6-[3-(trifluoromethyl)phenyl]pyridazine and 3 ml of 2-amino-1-propanol was heated at 130° C. for 24 hours, cooled and poured into water. The mixture was extracted with three 20 ml portions of dichloromethane. The combined extracts were washed with water, dried over magnesium sulfate and concentrated. The residual oil was dissolved in ethyl acetate and the solution passed through a short pad of silica gel. The filtrate was concentrated in vacuo and the residue was crystallized from dichloromethane-hexane to give 0.3 g of 2-[[6-[3-(trifluoromethyl)phenyl]-3-pyridazinyl]amino]-1-propanol as white crystals, mp 143°-144° C.

Workup

  1. temperaturecooled
  2. extractionThe mixture was extracted with three 20 ml portions of dichloromethane
  3. washThe combined extracts were washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. dissolutionThe residual oil was dissolved in ethyl acetate
  7. concentrationThe filtrate was concentrated in vacuo
  8. customthe residue was crystallized from dichloromethane-hexane

Sources & evidence

ORD record
ord-c67ee255125542b7bef92f122872e97e
Source dataset
uspto-grants-1986_02
Patent number
US04569934

Reaction notes

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