Hydrochloric Acid → HCID 178489168, compound

HRID 2230670Notes

Reaction equation

HRID 2230670 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]([C:12]2[NH:16][N:15]=[N:14][N:13]=2)=[CH:8][C:4]=1[C:5]([O-:7])=[O:6].[OH-].[Li+].Cl.ClCCl.CO>CO>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]([C:12]2[NH:13][N:14]=[N:15][N:16]=2)=[CH:8][C:4]=1[C:5]([OH:7])=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium Hydroxide2×HCID 21226129Dichloromethane methanol3×HCID 178489167HCID 178489167, compound

Product 1

HCID 178489168HCID 178489168, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Alternately, combine 2-methoxy-5-(1H-tetrazol-5-yl)benzoate (1.71 g, 7.3 mmol) and an aqueous solution of lithium hydroxide (25 mL, 1 M) in methanol (40 mL). After 18 hours, heat to reflux. After 1 hour, add an aqueous solution of lithium hydroxide (15 mL, 1 M) and continue the reflux. After 15 hours, cool to ambient temperature, acidify with a 1 M aqueous hydrochloric acid solution and extract four times with ethyl acetate and then with dichloromethane. Combine the organic layers, dry over MgSO4, filter and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting sequentially with dichloromethane/methanol 70/30, dichloromethane/methanol 50/50, dichloromethane/methanol 30/70, and then methanol to give the title compound.

Workup

  1. temperatureheat to reflux
  2. waitAfter 1 hour
  3. waitAfter 15 hours
  4. extractionextract four times with ethyl acetate
  5. dry with materialdry over MgSO4
  6. filtrationfilter
  7. customevaporate in vacuo
  8. customto give a residue

Sources & evidence

ORD record
ord-daf5833896014a05a28d7fc576afa70f
Source dataset
uspto-grants-2002_07
Patent number
US06423704B1

Reaction notes

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