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

HRID 1469739노트

반응식

HRID 1469739 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 21892291Methanol tetrahydrofuran water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-2660a89818e94e2b940a2c5ee5d25828
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006257B2

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