Ethanol → HCID 131720457, compound

HRID 861319Notes

Reaction equation

HRID 861319 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]([C:38](=[N:42][OH:43])[C:39]([OH:41])=[O:40])[C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]3[CH:37]=[CH:36][C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[N:29]=3)=[CH:22][CH:21]=2)=[CH:15][CH:14]=1.C(O)C.C1COCC1.[OH-].[Na+:53]>O>[Na+:53].[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]([C:38](=[N:42][OH:43])[C:39]([O-:41])=[O:40])[C:20]2[CH:21]=[CH:22][C:23]([O:26][CH2:27][C:28]3[CH:37]=[CH:36][C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[N:29]=3)=[CH:24][CH:25]=2)=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 73649701HCID 73649701, compound

Product 1

HCID 131720457HCID 131720457, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of bis(4-(2-quinolylmethoxy)phenyl)methyloximinoacetic acid (570 mg, 1.00 mmol), prepared as in step 1, ethanol (7 mL), dry THF (3 mL), and 1N NaOH (1.10 mL, 1.10 mmol) was stirred for 1 hour. The reaction mixture was diluted with water and the aqueous phase was washed with hexane and concentrated in vacuo. The resulting solid was collected by filtration to provide bis(4-(2-quinolylmethoxy)phenyl)methyloximinoacetic acid sodium salt (0.48 g, 81%): 1H NMR (300 MHz, DMSO-d6)δ4.18 (s, 2H), 5.38 (s, 2H), 5.42 (s, 2H), 7.05 (d, 2H, J=8.8 Hz), 7.10 (d, 2H, J=8.8 Hz), 7.29 (d, 2H, J=8.8 Hz), 7.29 (d, 2H, J=8.8 Hz), 7.57 (d, 2H, J=8.8 Hz), 7.62 (m, 2H), 7.69 (m, 2H), 7.79 (m, 2H), 8.02 (m, 2H), 8.43 (m, 2H); MS (FAB+) m/z: 592 (M+H)+. Anal. Calcd. for C33 H26N3O5Na: C, 69.83; H, 4.61; N, 7.40. Found: C, 68.77; H, 4.29; N, 6.74.

Workup

  1. washthe aqueous phase was washed with hexane
  2. concentrationconcentrated in vacuo
  3. filtrationThe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-a85b977af62a4120bd0745d598407715
Source dataset
uspto-grants-1998_02
Patent number
US05714488

Reaction notes

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