4-Nitro-1,3-benzenediamine → 4-Bromo-6-nitro-benzene-1,3-diamine dihydrobromide salt

HRID 449238

Reaction equation

HRID 449238 reaction equation
[Br:1]Br.[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][C:7]=1[NH2:13])([O-:5])=[O:4]>O1CCOCC1>[BrH:1].[BrH:1].[Br:1][C:10]1[CH:11]=[C:6]([N+:3]([O-:5])=[O:4])[C:7]([NH2:13])=[CH:8][C:9]=1[NH2:12]

Participants

4

Reactant 2

HCID 212084-Nitro-1,3-benzenediamineHCID 24408Bromine

Product 1

HCID 689804094-Bromo-6-nitro-benzene-1,3-diamine dihydrobromide salt

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The reaction scheme (CCLXIX) illustrates a synthetic process rthat included dropwise adding of 6.4 g bromine (40 mmol) to a solution of 4-nitrobenzene-1,3-diamine (5.56 g, 36.3 mmol), in 50 mL 1,4-dioxane, followed by stirring the solution was room temperature for 16 h. The yellow precipitate was isolated by filtration, washed with 1,4-dioxane (30 mL) and dried in vacuo to give 4-bromo-6-nitro-benzene-1,3-diamine dihydrobromide salt designated on the reaction scheme (CCLXIX) as compound 13 (8 g, 95%).

Workup

  1. customThe reaction scheme (CCLXIX)
  2. customThe yellow precipitate was isolated by filtration
  3. washwashed with 1,4-dioxane (30 mL)
  4. customdried in vacuo

Sources & evidence

ORD record
ord-c53e1a6c5ab04b069858c1509f90f74a
Source dataset
uspto-grants-2013_07
Patent number
US08481536B2

Linked notes

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