Lithium Hydroxide → Clt-28643

HRID 1042331Notes

Reaction equation

HRID 1042331 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20](=[O:23])[NH:21][CH3:22])[CH:18]=3)[N:13]=[CH:12][C:11]=2[C:24]([O:26]CC)=[O:25])=[CH:5][CH:4]=1.[Li+].[OH-]>CO.C1COCC1.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20](=[O:23])[NH:21][CH3:22])[CH:18]=3)[N:13]=[CH:12][C:11]=2[C:24]([OH:26])=[O:25])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 25020059Ethyl 4-[(4-methoxyphenyl)amino]-6-(methylcarbamoyl)quinoline-3-carboxylate

Product 1

HCID 42596938Clt-28643Yield 76.7%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Ethyl 4-[(4-methoxyphenyl)amino]-6-(methylcarbamoyl)quinoline-3-carboxylate (0.2 g) was stirred with LiOH (85.5 mg) in 6 mL of MeOH:THF:H2O (2:2:2) overnight. The reaction mixture was concentrated and the aqueous layer was washed with ethyl acetate. The aqueous layers were collected and acidified with aqueous HCl and the precipitate formed was filtered and dried to give 0.142 g (60%) of 4-[(4-methoxyphenyl)amino]-6-(methylcarbamoyl)-quinoline-3-carboxylic acid. 1H NMR (300 MHz, CD3OD) δ 9.05 (s, 1H, aromatic), 8.20 (s, 1H, aromatic), 8.12-7.81 (m, 2H, aromatic), 7.27 (d, 2H, J=9.9 Hz, aromatic), 7.06 (d, 2H, J=9.9 Hz, aromatic), 3.88 (s, 1H, —OCH3), 2.82 (s, 3H, —NCH3); LC-MS (m/z) 352.0 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. washthe aqueous layer was washed with ethyl acetate
  3. customThe aqueous layers were collected
  4. customthe precipitate formed
  5. filtrationwas filtered
  6. customdried

Sources & evidence

ORD record
ord-be1924281d8a418598a284d6640f07b6
Source dataset
uspto-grants-2013_10
Patent number
US08557843B2

Reaction notes

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