Hydrogen Bromide → 1-Bromophenanthren-2-amine

HRID 68531Notes

Reaction equation

HRID 68531 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][C:13]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH:6]=[CH:5][C:4]=2[CH:3]=1.[BrH:16].O.N>O>[NH2:1][C:2]1[CH:15]=[CH:14][C:13]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH:6]=[CH:5][C:4]=2[C:3]=1[Br:16]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 768932-PhenanthrenamineHCID 12896473Azane;hydrate

Product 1

HCID 2850291-Bromophenanthren-2-amineYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

First, 10.0 g of 2-aminophenanthrene were dissolved in 75 mL of N,N-dimethyl sulfoxide, and then 8.3 g of 48% hydrobromic acid were dropped to the solution over 4 hours while the solution was stirred at room temperature. The mixture was continuously stirred at room temperature for 20 hours, and was then stirred at 100° C. for 1 hour under heat. After having been cooled to room temperature, the reaction solution was poured into 300 mL of water. After the mixed solution had been neutralized with ammonia water, the crystal was separated by filtration. The resultant solid was recrystallized with ethanol and water. Thus, 12.6 g of a colorless crystal were obtained (in 90% yield).

Workup

  1. stirringThe mixture was continuously stirred at room temperature for 20 hours
  2. stirringwas then stirred at 100° C. for 1 hour
  3. temperatureunder heat
  4. temperatureAfter having been cooled to room temperature
  5. customthe crystal was separated by filtration
  6. customThe resultant solid was recrystallized with ethanol and water

Sources & evidence

ORD record
ord-93548f78cfc944d98d35ba3b27d30c9b
Source dataset
uspto-grants-2014_09
Patent number
US08822041B2

Reaction notes

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