Reaction #936

Reaction equation

2-fluoro-6-[(3-methoxyphenyl)sulfinyl]benzonitrile

2-Fluoro-6-[(3-methoxyphenyl)sulfinyl]benzonitrile

NH4OH

→

2-Amino-6-[(3-methoxyphenyl)sulfinyl]benzonitrile

Solvents

MeOH EtOH

Conditions

Workup

1. 1
   OtherThis mixture was sealed in a glass-lined bomb
2. 2
   OtherAfter solvent removal
3. 3
   Concentrationthe resultant concentrate
4. 4
   Otherwas purified by flash column chromatography on silica gel with 5% MeOH in methylene chloride as the eluent
5. 5
   OtherThis resulted in 0.36 g (53%) of 2-amino-6-[(3-methoxyphenyl)sulfinyl]benzonitrile as a solid

Procedure

To a solution of 0.73 g (2.7 mmol) of 2-fluoro-6-[(3-methoxyphenyl)sulfinyl]benzonitrile (Example 16) in 65 ml of MeOH/EtOH (2.5:4) was added 20 mL of concentrated NH4OH. This mixture was sealed in a glass-lined bomb and heated at 130° C. for 3 h. After solvent removal, the resultant concentrate was purified by flash column chromatography on silica gel with 5% MeOH in methylene chloride as the eluent. This resulted in 0.36 g (53%) of 2-amino-6-[(3-methoxyphenyl)sulfinyl]benzonitrile as a solid: mp 110°-114° C.; NMR. (Me2SO-d6, 200 MHz): δ 3.8 (s, 3H), 6.5 (br s, 2H); 7.1 (apparent d, 1H), 7.0 (apparent d, 2H), 7.2-7.3 (m, 2H), 7.5 (apparent t, 2H); mass spec (CI) 273 (M+ +1, 100%). Anal. Calc. for C14H12N2O2S: C, 61.75; H, 4.44; N, 10.29; S, 11.77. Found: C 61.65; H, 4.46; N, 10.21; S, 11.69.

Source