Hydrochloric Acid → N-Phenylnaphthalen-1-amine--hydrogen chloride (1/1)

HRID 1069173Notes

Reaction equation

HRID 1069173 reaction equation
[C:1]1([NH:7][C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:18]>CCOCC>[ClH:18].[C:1]1([NH:7][C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 7013Phenyl-1-naphthylamine

Product 1

HCID 21191506N-Phenylnaphthalen-1-amine--hydrogen chloride (1/1)Yield 60%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

In a 15 ml round bottom flask was placed N-phenyl-1-naphthylamine (1.41 g, 6.44 mmol) which was distilled at reduced pressure to produce a light purple oil with protruding white crystalline mounds. This suspension was dissolved in ether (50 ml) and cooled in an ice bath. To the cooled solution was added ether (25 ml) saturated with HCl gas to afford a light purple solid which was collected and dried. The purple solid was then dissolved in MeOH (20 ml) with heat and allowed to sit undisturbed to form light pink leaflets of the HCl salt (963 mg, 3.77 mmol, 60%) m.p. 164-167° C.

Workup

  1. customIn a 15 ml round bottom flask was placed
  2. customto produce a light purple oil
  3. temperaturecooled in an ice bath
  4. customto afford a light purple solid which
  5. customwas collected
  6. customdried
  7. dissolutionThe purple solid was then dissolved in MeOH (20 ml)
  8. temperaturewith heat

Sources & evidence

ORD record
ord-75b983d4c16c45c6b11a6b53b13b94e4
Source dataset
uspto-grants-2001_06
Patent number
US06251948B1

Reaction notes

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