1-Methyl-5-(4-nitrophenyl)-1H-tetrazole → 4-(1-methyl-1H-1,2,3,4-tetrazol-5-yl)aniline

HRID 395369Notes

Reaction equation

HRID 395369 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=2)=[N:5][N:4]=[N:3]1>[OH-].[OH-].[Pd+2].CO.CCOC(C)=O>[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=2)=[N:5][N:4]=[N:3]1

Participants

4

Reactant 1

HCID 126725461-Methyl-5-(4-nitrophenyl)-1H-tetrazole

Product 1

HCID 222590184-(1-methyl-1H-1,2,3,4-tetrazol-5-yl)anilineYield 95.4%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

1-Methyl-5-(4-nitro-phenyl)-1H-tetrazole (470 mg), 20% Pd(OH)2 (94 mg), and 1:1 MeOH/EtOAc (25 ml), were hydrogenated at 50 PSI for 1 hour. The reaction was filtered through fiberglass filter paper under nitrogen. The filtrate was stripped to yield 383 mg of yellow solids as product. Mass Spec detects 176 (M+H). NMR (300 MHz, CDCl3) δ 7.57 (d, 2H, J=7 Hz), 6.80 (d, 2H, J=7 Hz), 4.14 (s, 3H), 4.03 (M, 2H).

Workup

  1. filtrationThe reaction was filtered through fiberglass
  2. filtrationfilter paper under nitrogen

Sources & evidence

ORD record
ord-1bbe66f9252e49aeb226c74e59cf55e5
Source dataset
uspto-grants-2003_08
Patent number
US06605623B1

Reaction notes

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