Citric Acid → 8-Bromo-4-((4-methoxybenzyl)amino)quinoline-3-carboxylic acid

HRID 1469739Notes

Reaction equation

HRID 1469739 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([C:12]([O:14]CC)=[O:13])=[C:7]2[NH:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1.O[Li].O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.CO.O>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([C:12]([OH:14])=[O:13])=[C:7]2[NH:17][CH2:18][C:19]1[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 168937Lithium hydroxide, monohydrateHCID 86692233Ethyl 8-bromo-4-((4-methoxybenzyl)amino)quinoline-3-carboxylate

Product 1

HCID 866922348-Bromo-4-((4-methoxybenzyl)amino)quinoline-3-carboxylic acidYield 89.4%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of ethyl 8-bromo-4-((4-methoxybenzyl)amino)quinoline-3-carboxylate (1.2 g, 2.89 mmol) in THF-MeOH—H2O (10:7:3, 20 mL) was added LiOH—H2O (452 mg, 10.77 mmol) and the reaction mixture was stirred at rt for 12 h. Then the reaction mixture was acidified with citric acid and the organic volatiles were removed. The residue was extracted with EtOAc. The organic layer was washed with brine, separated, dried, filtered and concentrated to afford 1.0 g of the title product. 1H NMR (300 MHz, DMSO d6): δ 8.96 (s, 1H), 8.42-8.39 (d, J=8.7 Hz, 1H), 8.11-8.09 (d, J=7.2 Hz, 1H), 7.35-7.30 (m, 3H), 6.95-6.92 (d, J=8.7 Hz, 2H), 4.91 (s, 2H), 3.74 (s, 3H).

Workup

  1. customthe organic volatiles were removed
  2. extractionThe residue was extracted with EtOAc
  3. washThe organic layer was washed with brine
  4. customseparated
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2660a89818e94e2b940a2c5ee5d25828
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

Loading…