Stannous Chloride → 1-methyl-1H-1,2,3-benzotriazol-5-amine

HRID 2095158Notes

Reaction equation

HRID 2095158 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][C:9]([N+:11]([O-])=O)=[CH:10][C:5]=2[N:4]=[N:3]1.Cl[Sn]Cl>Cl>[NH2:11][C:9]1[CH:8]=[CH:7][C:6]2[N:2]([CH3:1])[N:3]=[N:4][C:5]=2[CH:10]=1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 3352691H-Benzotriazole, 1-methyl-5-nitro-

Product 1

HCID 2261971-methyl-1H-1,2,3-benzotriazol-5-amineYield 68.7%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

1-Methyl-5-nitrobenzotriazole (0.7 g) was reduced by SnCl2 (4.0 g) at 0° C. in 5 mL of conc. HCl. The pH of the reaction mixture was adjusted to basic and the mixture was extracted with EtOAc. The product 5-amino-1-methylbenzotriazole (0.4 g) obtained after removal of the solvent was used for the next reaction without further purification.

Workup

  1. extractionwas extracted with EtOAc

Sources & evidence

ORD record
ord-618aa8567c664f0697fa0b745555645a
Source dataset
uspto-grants-2013_05
Patent number
US08445694B2

Reaction notes

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