2-Aminophenol → HCID 22145448, compound

HRID 1825282Notes

Reaction equation

HRID 1825282 reaction equation
Cl.CN([CH:5]([CH3:15])[C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[CH:9]=1)=[O:7])C.[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[OH:23]>C(O)C>[ClH:14].[OH:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[NH:16][CH2:15][CH2:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[CH:9]=1)=[O:7]

Participants

4

Reactant 2

HCID 58012-AminophenolHCID 695907691-(3-Chlorophenyl)-2-(dimethylamino)propan-1-one hydrochloride (1:1)

Product 1

HCID 22145448HCID 22145448, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Dimethylamino-m-chloropropiophenone hydrochloride (74.9 g, 0.30 mol) was dissolved in 50% aqueous ethanol (700 ml) at reflux. 2-Aminophenol (32.9 g, 0.30 mol) was then added and the resulting red solution was refluxed for a further 2 hours. The reaction mixture was allowed to cool to room temperature and then extracted twice with ethyl acetate (2×100 ml). Note that brine was also added at this point to allow the two layers to separate effectively). The organic extracts were combined and an excess of concentrated hydrochloric acid (47 ml) was added. The solution was concentrated in vacuo and then allowed to cool. The precipitate that formed was filtered of, washed with diethyl ether and dried in vacuo to yield a cream powder (38.1 g, 40%).

Workup

  1. temperatureat reflux
  2. temperaturethe resulting red solution was refluxed for a further 2 hours
  3. extractionextracted twice with ethyl acetate (2×100 ml)
  4. additionwas also added at this point
  5. customto separate effectively)
  6. additionan excess of concentrated hydrochloric acid (47 ml) was added
  7. concentrationThe solution was concentrated in vacuo
  8. temperatureto cool
  9. customThe precipitate that formed
  10. filtrationwas filtered of,
  11. washwashed with diethyl ether
  12. customdried in vacuo

Sources & evidence

ORD record
ord-ef166bc45eec4d449b71bd9ae329f07e
Source dataset
uspto-grants-2006_05
Patent number
US07045624B2

Reaction notes

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