Hydrochloric Acid → HCID 131733189, compound

HRID 2208631Notes

Reaction equation

HRID 2208631 reaction equation
[C:1]1([N:7]([C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=2)N)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[Cl:20]([OH:24])(=[O:23])(=[O:22])=[O:21]>C(O)C>[Cl:20]([O-:24])(=[O:23])(=[O:22])=[O:21].[CH3:12][C:11]1([CH3:16])[C:10]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=3[CH:17]=[CH:18][C:9]=2[N+:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[C:10]1[CH3:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24247Perchloric AcidHCID 413288Hydrazine, 1-(2-naphthalenyl)-1-phenyl-

Product 1

HCID 131733189HCID 131733189, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-Phenyl-N-(2-naphthyl)hydrazine (2.3 g) (or hydrochloride (2.7 g)) was dissolved in 50 ml of ethanol and 10 g of 3-methyl-butanone-2 was added. To this mixture 10 ml 70% perchloric acid was added slowly with stirring at room temperature. Stirring was continued for one hour at 80-90° C. and after cooling down, the resultant precipitate was filtered off and washed with ethanol to provide 0.6 g (16%) 1,1,2-trimethyl-3-phenyl-1H-benzo[e]indolium perchlorate as a yellow solid, which was sufficiently pure for the next synthetic step. 1H NMR (400 MHz, TFA) δ 8.05 (d, 1H, J=8.5), 7.86 (t, 2H, J=7.6), 7.62 (dd, 4H, J=6.8, 13.4), 7.52 (t, 1H, J=7.6), 7.37 (d, 2H, J=7.3), 7.00 (d, 1H, J=8.9), 2.58 (s, 3H), 1.81 (s, 6H).

Workup

  1. stirringStirring
  2. temperatureafter cooling down
  3. filtrationthe resultant precipitate was filtered off
  4. washwashed with ethanol

Sources & evidence

ORD record
ord-aab0609da2204c32bfbd871a81b952b4
Source dataset
uspto-grants-2016_06
Patent number
US09376568B2

Reaction notes

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