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

HRID 1290140Notes

Reaction equation

HRID 1290140 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-b6e3bef9bf9a47e39e1d9968666e2f33
Source dataset
uspto-grants-1998_05
Patent number
US05750705

Reaction notes

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