Ammonia → HCID 22101788, compound

HRID 1458242Notes

Reaction equation

HRID 1458242 reaction equation
[NH3:1].[Cl:2][C:3]1[C:4]([O:14][CH3:15])=[N:5][C:6](F)=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1>C(O)C>[NH2:1][C:6]1[C:7]([C:9]([F:12])([F:11])[F:10])=[CH:8][C:3]([Cl:2])=[C:4]([O:14][CH3:15])[N:5]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 22101786HCID 22101786, compound

Product 1

HCID 22101788HCID 22101788, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
110 °C

Procedure

16.2 g (0.954 mol) of gaseous ammonia were injected into an autoclave containing 36.5 g (0.159 mol) of 3-chloro-6-fluoro-2-methoxy-5-trifluoromethylpyridine and 150 ml of ethanol and the mixture was then stirred for 15 hours at 110° C. After cooling and releasing the pressure, the reaction mixture was concentrated and the residue was partitioned in methylene chloride/water. After 0.4 g of insoluble matter had been separated off, the organic phase was separated off, and the aqueous phase was reextracted twice using methylene chloride. The organic extracts were dried and concentrated, giving 30.6 g (85% of theory) of the title compound as an oil. NMR (400 MHz, CDCl3) δ 7.6 pyr (1/s); 3.95 CH3O (3/s); 4.9 NH2 (2/s). After silica gel chromatography with methylene chloride, a further 33.2 g (72% of theory) of the title compound were obtained as a colorless oil of ηD24 =1.5140 (Table II, No. 2.001).

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture was concentrated
  3. customthe residue was partitioned in methylene chloride/water
  4. customAfter 0.4 g of insoluble matter had been separated off
  5. customthe organic phase was separated off
  6. customThe organic extracts were dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2210f37fe4094d6eaf634293142d7870
Source dataset
uspto-grants-1998_12
Patent number
US05849920

Reaction notes

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