HCID 13596127, compound → HCID 178521988, compound

HRID 325717Notes

Reaction equation

HRID 325717 reaction equation
C([N:8]1[C:12]([C:13]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:22]CC2C=CC=CC=2)=[O:14])=[N:11][N:10]=[N:9]1)C1C=CC=CC=1>C(O)(=O)C.[Pd]>[OH:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[NH:15][C:13]([C:12]1[NH:11][N:10]=[N:9][N:8]=1)=[O:14]

Participants

4

Reactant 1

HCID 13596127HCID 13596127, compound

Product 1

HCID 178521988HCID 178521988, compoundYield 42.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 1-benzyl-2'-benzyloxy-1H-tetrazole-5-carboxanilide (2.0 g) in glacial acetic acid (100 ml) was hydrogenated at 53° C. and 4.1 kg/cm2 for 18.5 hours, using a catalyst of palladium on charcoal (5% w/w). The mixture was filtered and the filtrate was evaporated at 40° C. in vacuo. The resulting solid was dissolved in a minimum volume of aqueous ammonia solution (2 N). The solution was filtered and then acidified with dilute hydrochloric acid (2 N). The resulting solid was filtered off, dried and recrystallised from aqueous dimethylformamide to give 2'-hydroxytetrazole-5-carboxanilide (0.45 g), m.p. 220°-223° C.

Workup

  1. customwas hydrogenated at 53° C.
  2. filtrationThe mixture was filtered
  3. customthe filtrate was evaporated at 40° C. in vacuo
  4. dissolutionThe resulting solid was dissolved in a minimum volume of aqueous ammonia solution (2 N)
  5. filtrationThe solution was filtered
  6. filtrationThe resulting solid was filtered off
  7. customdried
  8. customrecrystallised from aqueous dimethylformamide

Sources & evidence

ORD record
ord-2638b32a378041b78a0147fd7a8656a3
Source dataset
uspto-grants-1984_04
Patent number
US04442115

Reaction notes

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