3-(1-Methyl-1H-tetrazol-5-yl)-5-nitro-benzoic acid ethyl ester → 3-Amino-5-(1-methyl-1H-tetrazol-5-yl)-benzoic acid ethyl ester

HRID 1422410Notes

Reaction equation

HRID 1422410 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[C:5]1[CH:10]=[C:9]([N+:11]([O-])=O)[CH:8]=[C:7]([C:14]2[N:18]([CH3:19])[N:17]=[N:16][N:15]=2)[CH:6]=1)[CH3:2]>CCOC(C)=O.C(O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:20])[C:5]1[CH:6]=[C:7]([C:14]2[N:18]([CH3:19])[N:17]=[N:16][N:15]=2)[CH:8]=[C:9]([NH2:11])[CH:10]=1)[CH3:2]

Participants

4

Reactant 1

HCID 667334013-(1-Methyl-1H-tetrazol-5-yl)-5-nitro-benzoic acid ethyl ester

Product 1

HCID 667334833-Amino-5-(1-methyl-1H-tetrazol-5-yl)-benzoic acid ethyl esterYield 72.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

A solution of 3-(1-Methyl-1H-tetrazol-5-yl)-5-nitro-benzoic acid ethyl ester (6.5 g) in EtOAc:ethanol (1:1, 320 ml) was hydrogenated at 20° C. and 50 psi with 10% Pd/C (750 mg). After reaction completion, the mixture was filtered and the filtrate concentrated in vacuum to give the title compound (4.2 g). Rt=1.21 min (method D).

Workup

  1. customwas hydrogenated at 20° C.
  2. customAfter reaction completion
  3. filtrationthe mixture was filtered
  4. concentrationthe filtrate concentrated in vacuum

Sources & evidence

ORD record
ord-09c60ed909ab4da4b35ee6add0eea841
Source dataset
uspto-grants-2015_01
Patent number
USRE045323E1

Reaction notes

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