Hydrochloric Acid → (2-(5-Methyl-1H-tetrazol-1-yl)phenyl)methanamine hydrochloride

HRID 1749398Notes

Reaction equation

HRID 1749398 reaction equation
[CH3:1][C:2]1[N:6]([C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=2[C:9]#[N:10])[N:5]=[N:4][N:3]=1.[ClH:15]>CO.[Pd]>[ClH:15].[CH3:1][C:2]1[N:6]([C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=2[CH2:9][NH2:10])[N:5]=[N:4][N:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 1181620962-(5-methyl-1H-tetrazol-1-yl)benzonitrile

Product 1

HCID 118162087(2-(5-Methyl-1H-tetrazol-1-yl)phenyl)methanamine hydrochlorideYield 81%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-(5-methyl-1H-tetrazol-1-yl)benzonitrile (1.0 equiv.) in MeOH (0.4 M) was added palladium on charcoal and concentrated hydrochloric acid (1.0 equiv.). The reaction mixture was stirred at room temperature under hydrogen atmosphere (50 psi) overnight. After reaction completion, the mixture was filtered through celite. The filtrate was concentrated in vacuo to give the crude product (81% yield), which was used in the next step without further purification. 1H-NMR (400 MHz, CDCl3) δ (ppm) 7.85-7.75 (m, 3H), 7.66-7.64 (m, 1H), 3.96 (s, 2H), 2.60 (s, 3H); MS (ESI) m/z 190.1 [M+H]+.

Workup

  1. customAfter reaction completion
  2. filtrationthe mixture was filtered through celite
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-9216f85533774e6797fcabb1c63ceee8
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

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