HCID 178522682, compound → HCID 178522681, compound

HRID 614808Notes

Reaction equation

HRID 614808 reaction equation
C([O:8][C:9]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:10]=1[C:11]([NH:13][C:14]1[NH:18][N:17]=[N:16][N:15]=1)=[O:12])C1C=CC=CC=1>CN1CCCC1=O.[Pd]>[Cl:23][C:20]1[CH:21]=[CH:22][C:9]([OH:8])=[C:10]([CH:19]=1)[C:11]([NH:13][C:14]1[NH:18][N:17]=[N:16][N:15]=1)=[O:12]

Participants

4

Reactant 1

HCID 178522682HCID 178522682, compound

Product 1

HCID 178522681HCID 178522681, compoundYield 76.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 2-benzyloxy-5-chloro-N-(tetrazol-5-yl)benzamide (2.7 g) in N-methylpyrrolid-2-one (50 ml) was hydrogenated at 25° C. and 5 kg/cm2 pressure using a 5% w/w palladium on charcoal catalyst. The reaction mixture was filtered and then evaporated under vacuum and the resulting solid was triturated with water and then dried. This solid was boiled with ethanol (50 ml) for 10 minutes and the undissolved material was filtered off and washed with ethanol and with diethyl ether to give 5-chloro-2-hydroxy-N-(tetrazol-5-yl)benzamide (1.5 g), m.p. 266°-269° C. (with decomposition).

Workup

  1. customwas hydrogenated at 25° C.
  2. filtrationThe reaction mixture was filtered
  3. customevaporated under vacuum
  4. customthe resulting solid was triturated with water
  5. customdried
  6. filtrationthe undissolved material was filtered off
  7. washwashed with ethanol and with diethyl ether

Sources & evidence

ORD record
ord-ee5b6f97b6f247e5af603fa1c21de19b
Source dataset
uspto-grants-1979_03
Patent number
US04146631

Reaction notes

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