Reaction #70342

Reaction equation

5-methyl-2-(quinolin-3-ylamino)benzoic acid

→

desired compound

Yield 79.0%

5-methyl-2-(5,6,7,8-tetrahydroquinolin-3-ylamino)benzoic acid

Yield 79.0%

Solvents

TFA

Conditions

Workup

1. 1
   FiltrationAfter that the reaction mixture was filtered
2. 2
   Concentrationconcentrated
3. 3
   workup.DISSOLUTIONredissolved in water
4. 4
   workup.ADDITIONThe pH was adjusted to 4-5 by addition of 2N NaOH
5. 5
   Othera solid was formed
6. 6
   OtherThis yellow solid formed

Procedure

A solution of 5-methyl-2-(quinolin-3-ylamino)benzoic acid (Example 16) (1.08 mmol, 0.30 g) in TFA (2.5 ml) was hydrogenated under pressure (58 psi) with PtO2 (0.11 mmol, 0.028 g) as catalyst until all starting material disappeared. After that the reaction mixture was filtered, concentrated and redissolved in water. The pH was adjusted to 4-5 by addition of 2N NaOH and a solid was formed. This yellow solid formed was the desired compound (0.249 mg, 79% of yield).

Source