Ammonia → 2-Amino-3,6-dichloro-5-trifluoromethylpyridine

HRID 1458236Notes

Reaction equation

HRID 1458236 reaction equation
[NH3:1].[Cl:2][C:3]1[C:4](OC)=[N:5][C:6]([Cl:13])=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1>CO>[NH2:1][C:4]1[C:3]([Cl:2])=[CH:8][C:7]([C:9]([F:12])([F:11])[F:10])=[C:6]([Cl:13])[N:5]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 186895102,5-Dichloro-6-methoxy-3-trifluoromethylpyridine

Product 1

HCID 130641542-Amino-3,6-dichloro-5-trifluoromethylpyridineYield 28.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

12.4 g (0.73 mol) of gaseous ammonia were injected into a stirred mixture of 12.8 g (0.052 mol) of 3,6-dichloro-2-methoxy-5-trifluoromethylpyridine in 100 ml of methanol in an autoclave at 140° C., during which process the pressure climbed up to 200 bar. After half an hour, no starting material was detected in a sample. The reaction solution was concentrated and partitioned between methylene chloride and water. After drying, concentration, trituration of the residue with n-pentane, filtration with suction and drying, 3.4 g (28% of theory) of 2-amino-3,6-dichloro-5-trifluoromethylpyridine of m.p. 110°-112° C. were obtained. HPLC analysis revealed that the concentrated pentane filtrate (5 g) was composed of a further 19% of 2-amino-3,6-dichloro-5-trifluoromethylpyridine and 5 other compounds.

Workup

  1. waitAfter half an hour
  2. concentrationThe reaction solution was concentrated
  3. custompartitioned between methylene chloride and water
  4. customAfter drying
  5. concentrationconcentration, trituration of the residue
  6. filtrationwith n-pentane, filtration with suction
  7. customdrying

Sources & evidence

ORD record
ord-a191650a9ae64dbfb5880e128e45d91d
Source dataset
uspto-grants-1998_12
Patent number
US05849920

Reaction notes

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