Methanol → 2-Amino-3-chloro-6-methoxy-5-trifluoromethylpyridine
Reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([C:9]([F:12])([F:11])[F:10])=[C:4](Cl)[N:3]=1.[OH-:14].[K+].[CH3:16]O>CN(C)C=O>[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([C:9]([F:12])([F:11])[F:10])=[C:4]([O:14][CH3:16])[N:3]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 130 °C
Procedure
6.7 g (0.029 mol) of 2-amino-3,6-dichloro-5-trifluoromethylpyridine were added to a stirred mixture of 2.4 g (0.0377 mol) of 88% potassium hydroxide powder in 10 ml of methanol and 100 ml of dimethylformamide at 20° C. in the course of 5 minutes. The reaction mixture was now stirred for 89 hours at 130° C., with HPLC monitoring, a further 5 ml of methanol being added to the reaction mixture after 40 hours. After working-up in accordance with Example I.2., 0.3 g (4.6% of theory) of the title compound of ηD 24 =1.5143 was obtained in fractions 3 and 4. Fraction 5 contained 0.7 g (10% of theory) of 2-amino-3-chloro-6-dimethylamino-5-trifluoromethylpyridine (NMR 400 MHz, CDCl3 7.58 (pyridine), 2.95 (CH3)2N) and fractions 9-16 contained 1.1 g (16% of theory) of starting material. Other secondary components were found in the fractions which followed.
Sources & evidence
- ORD record
- ord-bf565feaf0ba45a9b9f926afdb023bec
- Source dataset
- uspto-grants-1998_05
- Patent number
- US05750705
Reaction notes
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