Hydrogen Bromide → HCID 19827562, compound

HRID 1974004Notes

Reaction equation

HRID 1974004 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9]C)=[CH:5][C:4]=1[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([NH2:18])[CH:13]=1.Br>>[NH2:18][C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][CH:15]=1)[CH2:11][C:4]1[CH:5]=[C:6]([OH:9])[CH:7]=[CH:8][C:3]=1[OH:2]

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 19827560HCID 19827560, compound

Product 1

HCID 19827562HCID 19827562, compoundYield 67%

Procedure

27 g of 1,4-dimethoxy-2-(3'-aminobenzyl)benzene prepared in (c) was mixed with a 46% hydrobromic acid aqueous solution. The mixture was refluxed on an oil bath for 1 to 2 hours. Since crystals deposited when cooled with ice, the filtration was carried out under cooling. The crystals were dissolved in 200 ml of water, and the resulting solution was neutralized by adding 25 g of sodium acetate. The free amine separated was recrystallized from an ethanol-benzene mixture to obtain 16 g of the subject compound. The melting point was 151° to 152° C.

Workup

  1. temperatureThe mixture was refluxed on an oil bath for 1 to 2 hours
  2. temperaturecooled with ice
  3. filtrationthe filtration
  4. temperatureunder cooling
  5. dissolutionThe crystals were dissolved in 200 ml of water
  6. additionby adding 25 g of sodium acetate
  7. customThe free amine separated
  8. customwas recrystallized from an ethanol-benzene mixture

Sources & evidence

ORD record
ord-8faa89f4da554cc58a8f9d9a2337a4df
Source dataset
uspto-grants-1976_12
Patent number
US03999991

Reaction notes

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