Reaction #934

Reaction equation

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

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

NH4OH

→

2-Amino-6-[(3-methoxyphenyl)sulfonyl]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 0.16 g (23%) of 2-amino-6-[(3-methoxyphenyl)sulfonyl]benzonitrile as a solid

Procedure

To a solution of 0.7 g (2.4 mmol) of 2-fluoro-6-[(3-methoxyphenyl)sulfonyl]benzonitrile (Example 14) in 110 ml of MeOH/EtOH (7:4) 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 0.16 g (23%) of 2-amino-6-[(3-methoxyphenyl)sulfonyl]benzonitrile as a solid: mp 186°-191° C.; NMR (Me2SO-d6, 200MHz) δ 3.82 (s, 3H), 6.6 (br s, 2H), 7.1 (apparent d, 1H), 7.2-7.7 (m, 6H); mass spec (CI) 289 (M+ +1, 100%). Anal. Calc. for C14H12N2 O3S: C, 58.32; H, 4.20;N, 9.72; S, 11.12. Found: C, 58.13; H, 4.17; N, 9.51; S, 10.95.

Source