4-Bromobenzene-1,2-diamine → HCID 178419336, compound

HRID 1051455Notes

Reaction equation

HRID 1051455 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([NH2:8])=[CH:6][CH:7]=1.[N:10]([O-])=O.[Na+]>O.CC(O)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[N:8]=[N:10][NH:9][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 3235934-Bromobenzene-1,2-diamineHCID 23668193Sodium Nitrite

Product 1

HCID 178419336HCID 178419336, compoundYield 137.7%

Reagents, catalysts & solvents 1

HCID 21899381Acetic acid--water (1/1)Solvent

Procedure

The mixture of 4-bromobenzene-1,2-diamine (200 mg, 1.1 mmol) and NaNO2 (569 mg, 5.3 mmol) in H2O/AcOH (5 mL/50 mL) was reacted at 80° C. for 6 hours. The mixture was concentrated, the residue was dissolved in DCM and extracted with water, and the organic phase dried by Na2SO4 and concentrated to give 300 mg of crude product which was used without further purification. LCMS (m/z): 198.1/199.1 [M+H]+/[M+2H]+

Workup

  1. customwas reacted at 80° C. for 6 hours
  2. concentrationThe mixture was concentrated
  3. dissolutionthe residue was dissolved in DCM
  4. extractionextracted with water
  5. dry with materialthe organic phase dried by Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4c691b4289d0471888d6fd9415579195
Source dataset
uspto-grants-2016_07
Patent number
US09388173B2

Reaction notes

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