Hydrochloric Acid → HCID 178427247, compound

HRID 614827Notes

Reaction equation

HRID 614827 reaction equation
FC(F)(F)C(O)=O.N1C(C)=CC=CC=1C.[C:16]([C:18]1[CH:26]=[C:25]([CH3:27])[CH:24]=[C:20]([C:21]([OH:23])=[O:22])[C:19]=1[OH:28])#[N:17].[N-:29]=[N+:30]=[N-:31].[Na+].[Cl-].[Li+].Cl>O>[CH3:27][C:25]1[CH:24]=[C:20]([C:21]([OH:23])=[O:22])[C:19]([OH:28])=[C:18]([C:16]2[NH:31][N:30]=[N:29][N:17]=2)[CH:26]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 79372,6-LutidineHCID 33557Sodium AzideHCID 433294Lithium ChlorideHCID 130269333-Cyano-2-hydroxy-5-methylbenzoic acid

Product 1

HCID 178427247HCID 178427247, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Trifluoroacetic acid (0.8 ml) was added to dry 2,6-lutidine (10 ml) and the mixture was then treated with 3-cyano-5-methylsalicylic acid (0.885 g), sodium azide (0.65 g) and lithium chloride (20 mg), and heated at reflux for 20 hours. The mixture was then diluted with water (20 ml) and acidified by treatment with concentrated hydrochloric acid. The resulting precipitate was collected and recrystallized from a large amount of acetic acid to give 5-methyl-3-(tetrazol-5-yl)salicylic acid (0.65 g), m.p. 290°-292° C. (with decomposition).

Workup

  1. temperatureheated
  2. temperatureat reflux for 20 hours
  3. customThe resulting precipitate was collected
  4. customrecrystallized from a large amount of acetic acid

Sources & evidence

ORD record
ord-8086c434d1574442bcc5d4a5a726eeed
Source dataset
uspto-grants-1979_03
Patent number
US04146631

Reaction notes

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