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

HRID 861323Notes

Reaction equation

HRID 861323 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH2:12][O:13][C:14]3[CH:19]=[CH:18][C:17]([CH:20]([C:40](=[N:44][OH:45])[C:41]([OH:43])=[O:42])[C:21]4[CH:26]=[CH:25][C:24]([O:27][CH2:28][C:29]5[CH:38]=[CH:37][C:36]6[C:31](=[CH:32][C:33]([Cl:39])=[CH:34][CH:35]=6)[N:30]=5)=[CH:23][CH:22]=4)=[CH:16][CH:15]=3)=[N:9]2)=[CH:4][CH:3]=1.[OH-].[Na+:47]>CCO.C1COCC1>[Na+:47].[Cl:39][C:33]1[CH:32]=[C:31]2[C:36]([CH:37]=[CH:38][C:29]([CH2:28][O:27][C:24]3[CH:23]=[CH:22][C:21]([CH:20]([C:40](=[N:44][OH:45])[C:41]([O-:43])=[O:42])[C:17]4[CH:16]=[CH:15][C:14]([O:13][CH2:12][C:8]5[CH:7]=[CH:6][C:5]6[C:10](=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=6)[N:9]=5)=[CH:19][CH:18]=4)=[CH:26][CH:25]=3)=[N:30]2)=[CH:35][CH:34]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 73649702Bis(4-(7-chloro-2-quinolylmethoxy)phenyl)methyloximinoacetic acid

Product 1

HCID 131720458Bis(4-(7-chloro-2-quinolylmethoxy)phenyl)methyloximinoacetic acid sodium saltYield 83.3%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To a solution in EtOH--THF (3:1, 4 mL) of bis(4-(7-chloro-2-quinolyl-methoxy)phenyl)methyloximinoacetic acid (240 mg, 0.4 mmol), prepared as in Example 5, was added 1N aqueous NaOH (0.5 mL, 0.5 mmol). The mixture was stirred overnight at room temperature and concentrated in vacuo. The residue was slurried in ether (15 mL), filtered, and dried in vacuo to provide bis(4-(7-chloro-2-quinolylmethoxy)phenyl)methyloximinoacetic acid sodium salt (220 mg): mp 181°-183° C.; 1H NMR (300 MHz, DMSO-d6)δ4.15 (s, 2H), 5.41 (m, 4H), 7.07 (dd, 4H, J=12, 3 Hz), 7.28 (d, 2H, J=9 Hz), 7.56 (d, 2H, J=9 Hz), 7.73 (m, 4H), 8.06 (m, 4H), 8.49 (m, 2H); MS (FAB) 660 (M+H)+, 682 (M+Na)+. Anal. Calcd. for C35H24Cl2N3O5Na×2.5 H2O: C, 59.58, H, 4.11; N, 5.96. Found C, 59.61; H, 3.94; N, 5.72.

Workup

  1. concentrationconcentrated in vacuo
  2. filtrationfiltered
  3. customdried in vacuo

Sources & evidence

ORD record
ord-ea49e35e0dcc49af9b8a655e44b9f387
Source dataset
uspto-grants-1998_02
Patent number
US05714488

Reaction notes

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