Ammonia → 5-(trifluoromethyl)pyridazin-3-amine

HRID 2046392Notes

Reaction equation

HRID 2046392 reaction equation
Cl[C:2]1[N:3]=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.C(O)(C)C.[NH3:16]>>[F:9][C:8]([F:11])([F:10])[C:6]1[CH:7]=[C:2]([NH2:16])[N:3]=[N:4][CH:5]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 3776IsopropanolHCID 592772973-Chloro-5-(trifluoromethyl)pyridazine

Product 1

HCID 671230995-(trifluoromethyl)pyridazin-3-amine

Conditions

Temperature
80 °C

Procedure

3-Chloro-5-(trifluoromethyl)pyridazine (28.0 g, 153 mmol) was dissolved in ammonia in isopropanol (200 mL, 400 mmol, 2.0 M) and heated at 80° C. in a pressure vessel for 3 days. The reaction was cooled to room temperature and concentrated under reduced pressure to take the isopropanol off. The residue was purified by flash chromatography to afford the title compound as an off white solid, 1H NMR (500 MHz, CDCl3) δ 8.83 (s, 1H); 6.91 (s, 1H); 5.00 (s, 2H, br). LRMS (APCI) calc'd for (CsH4F3N3) [M+H]+, 164.1. found 164.1.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-2ee1083c97a3410b8af19f34911c4c65
Source dataset
uspto-grants-2013_11
Patent number
US08592425B2

Reaction notes

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