3-bromo-5-nitrophenyl-1-methyl-1H-tetrazole → 3-Bromo-5-(1-methyl-1H-tetrazol-5-yl)-phenylamine

HRID 2059642Notes

Reaction equation

HRID 2059642 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:11]2[N:15]([CH3:16])[N:14]=[N:13][N:12]=2)[CH:5]=[C:6]([N+:8]([O-])=O)[CH:7]=1>CCOC(C)=O.[Ni]>[Br:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[C:4]([C:11]2[N:15]([CH3:16])[N:14]=[N:13][N:12]=2)[CH:3]=1

Participants

4

Reactant 1

HCID 222526903-bromo-5-nitrophenyl-1-methyl-1H-tetrazole

Product 1

HCID 667333043-Bromo-5-(1-methyl-1H-tetrazol-5-yl)-phenylamineYield 15.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-(3-Bromo-5-nitro-phenyl)-1-methyl-1H-tetrazole (2.1 g) in EtOAc (100 ml) was hydrogenated on a H-cube® apparatus at 20° C., room pressure with a flow rate of 1 ml/min using a Raney-Ni cartridge. After reaction completion, the mixture was concentrated in vacuum and triturated with MeOH. The solid was filtered and further triturated and air-dried to give the title compound (290 mg). Rt 1.25 min (method D).

Workup

  1. customwas hydrogenated on a H-cube® apparatus at 20° C.
  2. customAfter reaction completion
  3. concentrationthe mixture was concentrated in vacuum
  4. customtriturated with MeOH
  5. filtrationThe solid was filtered
  6. customfurther triturated
  7. customair-dried

Sources & evidence

ORD record
ord-88b0e23e12ae43cbb7db6fdda81be2c5
Source dataset
uspto-grants-2012_10
Patent number
US08278302B2

Reaction notes

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