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

HRID 1469739ノート

反応式

HRID 1469739 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 21892291Methanol tetrahydrofuran water溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-2660a89818e94e2b940a2c5ee5d25828
出典データセット
uspto-grants-2015_04
特許番号
US09006257B2

反応ノート

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