Lithium hydroxide, monohydrate → 4'-Methyl-5-tetrazol-1-yl-biphenyl-3-carboxylic acid

HRID 217323Notes

Reaction equation

HRID 217323 reaction equation
O[Li].O.C[O:5][C:6]([C:8]1[CH:9]=[C:10]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)[CH:11]=[C:12]([N:14]2[CH:18]=[N:17][N:16]=[N:15]2)[CH:13]=1)=[O:7]>O.C1COCC1>[CH3:25][C:22]1[CH:23]=[CH:24][C:19]([C:10]2[CH:11]=[C:12]([N:14]3[CH:18]=[N:17][N:16]=[N:15]3)[CH:13]=[C:8]([C:6]([OH:7])=[O:5])[CH:9]=2)=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 578511214'-Methyl-5-tetrazol-1-yl-biphenyl-3-carboxylic acid methyl ester

Product 1

HCID 578515114'-Methyl-5-tetrazol-1-yl-biphenyl-3-carboxylic acidYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of LiOH.H2O (1.86 g, 44.2 mmol) in H2O (40 mL) was added dropwise to a suspension of 4′-Methyl-5-tetrazol-1-yl-biphenyl-3-carboxylic acid methyl ester (10 g, 34 mmol) in THF (25 mL) at 0° C. The reaction mixture was allowed to warm to room temperature and was stirred until the reaction solution turned clear. Solvent was removed under vacuum and the aqueous solution was acidified by addition of 10% HCl to pH=3. The resulting precipitate was collected and dried to afford 4′-Methyl-5-tetrazol-1-yl-biphenyl-3-carboxylic acid as white solid (8.85 g, 93%). MS (M+H)=281.

Workup

  1. customSolvent was removed under vacuum
  2. additionthe aqueous solution was acidified by addition of 10% HCl to pH=3
  3. customThe resulting precipitate was collected
  4. customdried

Sources & evidence

ORD record
ord-39da45d3a24f4ddbb7d8780cd7a79b41
Source dataset
uspto-grants-2012_06
Patent number
US08193368B2

Reaction notes

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