5-Methyl-2-(quinolin-3-ylamino)benzoic acid → 5-Methyl-2-(5,6,7,8-tetrahydroquinolin-3-ylamino)benzoic acid

HRID 42064Notes

Reaction equation

HRID 42064 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([NH:11][C:12]2[CH:13]=[N:14][C:15]3[C:20]([CH:21]=2)=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]>C(O)(C(F)(F)F)=O.O=[Pt]=O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([NH:11][C:12]2[CH:13]=[N:14][C:15]3[CH2:16][CH2:17][CH2:18][CH2:19][C:20]=3[CH:21]=2)=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]

Participants

4

Reactant 1

HCID 251867215-Methyl-2-(quinolin-3-ylamino)benzoic acid

Product 1

HCID 468474275-Methyl-2-(5,6,7,8-tetrahydroquinolin-3-ylamino)benzoic acidYield 79%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 6422Trifluoroacetic acidSolvent

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).

Workup

  1. filtrationAfter that the reaction mixture was filtered
  2. concentrationconcentrated
  3. dissolutionredissolved in water
  4. additionThe pH was adjusted to 4-5 by addition of 2N NaOH
  5. customa solid was formed
  6. customThis yellow solid formed

Sources & evidence

ORD record
ord-ae17b7f92e9047fa9b704095ee8458a9
Source dataset
uspto-grants-2013_09
Patent number
US08536165B2

Reaction notes

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