Methanol → 3-(1-methyl-1H-1,2,3,4-tetrazol-5-yl)aniline

HRID 1169203Notes

Reaction equation

HRID 1169203 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-])=O)[CH:8]=2)=[N:5][N:4]=[N:3]1.CO>C(OCC)(=O)C.[Pd]>[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([NH2:13])[CH:8]=2)=[N:5][N:4]=[N:3]1

Participants

5

Reactant 2

HCID 887MethanolHCID 140450781-methyl-5-(3-nitrophenyl)-1H-Tetrazole

Product 1

HCID 144576753-(1-methyl-1H-1,2,3,4-tetrazol-5-yl)anilineYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

In a Paar flask 1-methyl-5-(3-nitrophenyl)-tetrazole (28.8 g, 140 mmol) was dissolved in ethyl acetate (430 mL) and methanol (1270 mL) and added to palladium on carbon (2.7 g, 10 wt %). The reaction mixture was hydrogenated for 1.5 hours with vigorous shaking. The reaction mixture was filtered, and concentrated in vacuo to give a white solid (24.0 g, 98%) was used with further purification. 1H NMR (300 MHz, CDCl3), δ: 7.21 (dd, J=8, J′=7, 1H), 6.99 (s, 1H), 6.90 (d, J=7, 1H), 6.76 (d, J=8, 1H), 5.44 (bs, 2H), 4.10 (s, 3H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-caa7646861f643ecb27883fbc437c2aa
Source dataset
uspto-grants-2003_09
Patent number
US06627629B2

Reaction notes

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