Lithium hydroxide, monohydrate → HCID 73649701, compound

HRID 861318Notes

Reaction equation

HRID 861318 reaction equation
O.[OH-].[Li+].O.C(O)C.C([O:10][C:11](=[O:52])[C:12]([CH:15]([C:34]1[CH:39]=[CH:38][C:37]([O:40][CH2:41][C:42]2[CH:51]=[CH:50][C:49]3[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=3)[N:43]=2)=[CH:36][CH:35]=1)[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]2[CH:33]=[CH:32][C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:25]=2)=[CH:18][CH:17]=1)=[N:13][OH:14])C>C1COCC1.C(O)C.O>[N:25]1[C:26]2[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:32]=[CH:33][C:24]=1[CH2:23][O:22][C:19]1[CH:20]=[CH:21][C:16]([CH:15]([C:12](=[N:13][OH:14])[C:11]([OH:52])=[O:10])[C:34]2[CH:35]=[CH:36][C:37]([O:40][CH2:41][C:42]3[CH:51]=[CH:50][C:49]4[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=4)[N:43]=3)=[CH:38][CH:39]=2)=[CH:17][CH:18]=1

Participants

7

Reactant 3

HCID 168937Lithium hydroxide, monohydrateHCID 19096565Water ethanolHCID 131720456HCID 131720456, compound

Product 1

HCID 73649701HCID 73649701, compoundYield 85.3%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide monohydrate (1.4 g, 33.4 mmol) in 1:1 water-ethanol (20 mL) was added a solution of bis(4-(2-quinolylmethoxy)phenyl)-methyloximinoacetic acid ethyl ester (8.5 g, 14.2 mmol), prepared as in Example 3, in THF (80 mL) and ethanol (10 mL). The turbid reaction was stirred for 1 hour, and then was diluted with water (80 mL). The aqueous layer was washed with 1:1 ether-hexane (50 mL) and then filtered to remove fine solids. The filtrate was acidified to pH 4 with 1N HCl, and the precipitated solid collected by filtration and dried in vacuo to give bis(4-(2-quinolylmethoxy)phenyl)methyloximinoacetic acid (6.9 g, 85%): mp 183°-185° C.

Workup

  1. customThe turbid reaction
  2. washThe aqueous layer was washed with 1:1 ether-hexane (50 mL)
  3. filtrationfiltered
  4. customto remove fine solids
  5. filtrationthe precipitated solid collected by filtration
  6. customdried in vacuo

Sources & evidence

ORD record
ord-3086f747225549acb98561644411a44c
Source dataset
uspto-grants-1998_02
Patent number
US05714488

Reaction notes

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