Stannous Chloride → 6-Amino-1-methyl-1H-benzotriazole

HRID 2095159Notes

Reaction equation

HRID 2095159 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[C:8]([N+:11]([O-])=O)[CH:9]=[CH:10][C:5]=2[N:4]=[N:3]1.Cl[Sn]Cl>Cl>[NH2:11][C:8]1[CH:9]=[CH:10][C:5]2[N:4]=[N:3][N:2]([CH3:1])[C:6]=2[CH:7]=1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 3352711H-Benzotriazole, 1-methyl-6-nitro-

Product 1

HCID 5904686-Amino-1-methyl-1H-benzotriazoleYield 90.2%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

3-Methyl-5-nitrobenzotriazole (0.8 g) was reduced by SnCl2 (4.5 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-3-methylbenzotriazole (0.6 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-8bcf20429ebd4d7ea47f3df2ff4df37a
Source dataset
uspto-grants-2013_05
Patent number
US08445694B2

Reaction notes

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