Ammonia → 5-Aminobenzene-1,3-diol

HRID 418975Notes

Reaction equation

HRID 418975 reaction equation
[OH:1][C:2]1[CH:7]=[C:6](O)[CH:5]=[C:4]([OH:9])[CH:3]=1.[NH3:10]>O>[OH:1][C:2]1[CH:7]=[C:6]([CH:5]=[C:4]([OH:9])[CH:3]=1)[NH2:10]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 359Phloroglucinol

Product 1

HCID 4107515-Aminobenzene-1,3-diolYield 37%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 200-mL, 2-necked flask was added 31.5 g (250 mmol) of 1,3,5-trihydroxybenzene. After replaced with argon, 25 mL of 28% ammonia and water were added thereto, and the resulting mixture was stirred in a water bath for 18 hours. Water was removed away in vacuo and 50 mL of isopropanol was added. The obtained mixture was ice-cooled for 2 hours to precipitate a solid and the precipitated solid was obtained by filtration. The solid was washed with isopropanol and then vacuum-dried, whereby a desired product was obtained (Quantity: 11.4 g, 91.3 mmol, Yield: 37%).

Workup

  1. additionwere added
  2. customWater was removed away in vacuo and 50 mL of isopropanol
  3. additionwas added
  4. temperaturecooled for 2 hours
  5. customto precipitate a solid
  6. customthe precipitated solid was obtained by filtration
  7. washThe solid was washed with isopropanol
  8. customvacuum-dried

Sources & evidence

ORD record
ord-bf61faecc2664dc69570e273eab33397
Source dataset
uspto-grants-2012_01
Patent number
US08093349B2

Reaction notes

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