Tetrahydrofuran → 6-(4-Biphenylylmethoxy)nicotinic Acid

HRID 1356447Notes

Reaction equation

HRID 1356447 reaction equation
[C:1]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15]C)=[O:14])=[CH:11][N:10]=2)=[CH:3][CH:2]=1.C1COCC1>CO.[OH-].[Na+].Cl>[C:1]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9]2[CH:18]=[CH:17][C:12]([C:13]([OH:15])=[O:14])=[CH:11][N:10]=2)=[CH:3][CH:2]=1

Participants

6

Reactant 2

HCID 8028TetrahydrofuranHCID 18508353Methyl 6-(4-biphenylylmethoxy)nicotinate

Product 1

HCID 178174806-(4-Biphenylylmethoxy)nicotinic AcidYield 83.7%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of methyl 6-(4-biphenylylmethoxy)nicotinate (2.0 g) in methanol (20 ml)/THF(40 ml) was added iN aqueous sodium hydroxide (13 ml) at room temperature. After stirring at room temperature for 4 hr the reaction mixture was diluted with 1 N hydrochloric acid (13 ml) and concentrated. The precipitate was collected by filtration and washed with water and diethyl ether sequentially to obtain the titled compound (1.6 g) as amorphous powder.

Workup

  1. concentrationconcentrated
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water and diethyl ether sequentially

Sources & evidence

ORD record
ord-dfbdd527ca69446aba9847ef571372c9
Source dataset
uspto-grants-2003_07
Patent number
US06586475B1

Reaction notes

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