Sodium Hydroxide → (+/-)-4-(1-((3-Methylquinolin-2-yl)amino)butyl)benzoic acid

HRID 1424246Notes

Reaction equation

HRID 1424246 reaction equation
[CH3:1][C:2]1[C:3]([NH:12][CH:13]([C:17]2[CH:27]=[CH:26][C:20]([C:21]([O:23]CC)=[O:22])=[CH:19][CH:18]=2)[CH2:14][CH2:15][CH3:16])=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[OH-].[Na+]>O1CCCC1.CO>[CH3:1][C:2]1[C:3]([NH:12][CH:13]([C:17]2[CH:18]=[CH:19][C:20]([C:21]([OH:23])=[O:22])=[CH:26][CH:27]=2)[CH2:14][CH2:15][CH3:16])=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 71243834Ethyl(+/-)-4-(1-((3-methylquinolin-2-yl)amino)butyl)benzoate

Product 1

HCID 71239463(+/-)-4-(1-((3-Methylquinolin-2-yl)amino)butyl)benzoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Intermediate 4 (34.29 g, 94.60 mmol) in tetrahydrofuran (234 mL) and methanol (234 mL) was added 1 N aq sodium hydroxide (473 mL). The solution was stirred at room temperature for 16 h. The solution was concentrated under reduced pressure to remove tetrahydrofuran and methanol. 3 N aqueous hydrochloric acid was added dropwise to pH 2. The resulting slurry was filtered, and the solid was washed with water (300 mL, then 100 mL). The solid was dried by azeotropic removal of water first with toluene, then heptane (7×100 mL), followed by heating to 70° C. under reduced pressure to afford (+/−)-4-(1-((3-methylquinolin-2-yl)amino)butyl)benzoic acid (Intermediate 5). 1H NMR (400 MHz, CD3OD) δ 8.09 (s, 1H), 8.02 (d, J=8.4 Hz, 2H), 7.84 (d, J=8.4 Hz, 1H), 7.72 (d, J=7.8 Hz, 1H), 7.66-7.58 (m, 3H), 7.40 (t, J=7.6 Hz, 1H), 5.56 (dd, J=6.0, 8.6 Hz, 1H), 2.49 (s, 3H), 2.24-2.10 (m, 1H), 2.08-1.95 (m, 1H), 1.66-1.52 (m, 1H), 1.52-1.39 (m, 1H), 1.03 (t, J=7.4 Hz, 3H).

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. customto remove tetrahydrofuran and methanol
  3. addition3 N aqueous hydrochloric acid was added dropwise to pH 2
  4. filtrationThe resulting slurry was filtered
  5. washthe solid was washed with water (300 mL
  6. dry with materialThe solid was dried by azeotropic removal of water first with toluene
  7. temperatureby heating to 70° C. under reduced pressure

Sources & evidence

ORD record
ord-9149399533054e5b91efaea63e44964c
Source dataset
uspto-grants-2015_01
Patent number
US08927577B2

Reaction notes

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