Hydrochloric Acid → HCID 178428935, compound

HRID 654362Notes

Reaction equation

HRID 654362 reaction equation
Cl.[CH3:2][C:3]1[C:8]([C:9]([O:11]CC)=[O:10])=[C:7]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:28]3[NH:32][N:31]=[N:30][N:29]=3)=[CH:18][CH:17]=2)[CH:6]=[C:5]([CH3:33])[N:4]=1.Cl>[OH-].[Na+]>[CH3:2][C:3]1[C:8]([C:9]([OH:11])=[O:10])=[C:7]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:28]3[NH:29][N:30]=[N:31][N:32]=3)=[CH:20][CH:21]=2)[CH:6]=[C:5]([CH3:33])[N:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178470020HCID 178470020, compound

Product 1

HCID 178428935HCID 178428935, compoundYield 32.4%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of ethyl 2,6-dimethyl-4-[(2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methoxy]pyridine-3-carboxylate hydrochloride (240 mg) in 2M aqueous sodium hydroxide (5 ml) was heated under reflux for 2 hours. The solution was cooled and acidified to pH 3 with 6M hydrochloric acid. The precipitated solid was collected by filtration and triturated with hot methanol to give 2,6-dimethyl-4-[(2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methoxy]pyridine-3-carboxylic acid (67 mg), as a white powder, m.p. 237° C.; NMR (d6 -DMSO, d4 -acetic acid): 2.45(s,3H), 2.55(s,3H), 5.3(s,2H), 7.1(s,1H), 7.2(d,2H), 7.4(d,2H), 7.4-7.75 (complex m,4H); mass spectrum (DMSO/GLY): 400 (M-H)-, 166; microanalysis, found: C,64.5; H,4.5; N,17.0%; C22H19N5O3.0.5H2O requires: C,64.5; H,4.9; N,17.1%.

Workup

  1. temperatureunder reflux for 2 hours
  2. temperatureThe solution was cooled
  3. filtrationThe precipitated solid was collected by filtration
  4. customtriturated with hot methanol

Sources & evidence

ORD record
ord-ad999d4915cd4f7f8321155ab59e1304
Source dataset
uspto-grants-1992_07
Patent number
US05130318

Reaction notes

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