Sodium Hydroxide → Bis(4-(7-chloro-2-quinolylmethoxy)phenyl)methyloximinoacetic acid

HRID 861322Notes

Reaction equation

HRID 861322 reaction equation
C([O:3][C:4](=[O:47])[C:5]([CH:8]([C:28]1[CH:33]=[CH:32][C:31]([O:34][CH2:35][C:36]2[CH:45]=[CH:44][C:43]3[C:38](=[CH:39][C:40]([Cl:46])=[CH:41][CH:42]=3)[N:37]=2)=[CH:30][CH:29]=1)[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][C:21]([Cl:27])=[CH:22][CH:23]=3)[N:18]=2)=[CH:11][CH:10]=1)=[N:6][OH:7])C.[OH-].[Na+]>C1COCC1.CCO.O>[Cl:46][C:40]1[CH:39]=[C:38]2[C:43]([CH:44]=[CH:45][C:36]([CH2:35][O:34][C:31]3[CH:30]=[CH:29][C:28]([CH:8]([C:5](=[N:6][OH:7])[C:4]([OH:47])=[O:3])[C:9]4[CH:10]=[CH:11][C:12]([O:15][CH2:16][C:17]5[CH:26]=[CH:25][C:24]6[C:19](=[CH:20][C:21]([Cl:27])=[CH:22][CH:23]=6)[N:18]=5)=[CH:13][CH:14]=4)=[CH:33][CH:32]=3)=[N:37]2)=[CH:42][CH:41]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86752020Bis(4-(7-chloro-2-quinolylmethoxy)phenyl)methyloximinoacetic acid ethyl ester

Product 1

HCID 73649702Bis(4-(7-chloro-2-quinolylmethoxy)phenyl)methyloximinoacetic acidYield 68.1%

Reagents, catalysts & solvents 1

HCID 18504229Ethanol tetrahydrofuran waterSolvent

Procedure

To a solution in THF/EtOH/H2O (3:2:1, 35 mL) of bis(4-(7-chloro-2-quinolylmethoxy)phenyl)methyloximinoacetic acid ethyl ester (0.66 g, 1 mmol), prepared as in step 2, was added aqueous 1N NaOH (5 mL. The mixture was stirred at room temperature for 18 hours, concentrated in vacuo, diluted with water, and neutralized with 6N HCl. The precipitated solid was collected by filtration and slurried in Et2O/hexane (1:1, 50 mL), filtered, and dried in vacuo to provide bis(4-(7-chloro-2-quinolylmethoxy)phenyl)methyloximinoacetic acid (435 mg): mp 201°-202° C.; 1H NMR (300 MHz, DMSO-d6)δ4.55 (s, 2H), 5.39 (s, 2H), 5.44 (s, 2H), 7.08 (d, 2H, J=9 Hz), 7.15 (d, 2H, J=9 Hz), 7.31 (d, 2H, J=9 Hz), 7.41 (d, 2H, J=9 Hz), 7.68 (m, 3H), 7.72 (d, 1H, J=9 Hz), 8.80 (m, 4H), 8.49 (t, 2H, J=9 Hz); MS (DCI/NH3) m/e 638 (M+H)+. Anal. Calcd. for C35H25 Cl2N3O5 ×H2O: C, 64.12; H, 4.12; N, 6.41. Found C, 64.44; H, 3.96; N, 6.30.

Workup

  1. concentrationconcentrated in vacuo
  2. additiondiluted with water
  3. filtrationThe precipitated solid was collected by filtration
  4. filtrationfiltered
  5. customdried in vacuo

Sources & evidence

ORD record
ord-e877c4dbfb8a46b2892c9ec12cb76f5b
Source dataset
uspto-grants-1998_02
Patent number
US05714488

Reaction notes

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