Hydrochloric Acid → 2-[(2,6-Dimethyl-4-aminophenyl)amino]-1-pyrroline, dihydrochloride

HRID 484788Notes

Reaction equation

HRID 484788 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[C:4]([CH3:11])[C:3]=1[NH:12][C:13]1[CH2:17][CH2:16][CH2:15][N:14]=1.[ClH:18].C(OCC)C>CO.C(O)(C)C>[ClH:18].[ClH:18].[CH3:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[C:4]([CH3:11])[C:3]=1[NH:12][C:13]1[CH2:17][CH2:16][CH2:15][N:14]=1

Participants

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 3283Diethyl EtherHCID 202723942-[(2,6-Dimethyl-4-nitrophenyl)amino]-1-pyrroline

Product 1

HCID 704660602-[(2,6-Dimethyl-4-aminophenyl)amino]-1-pyrroline, dihydrochloride

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3776IsopropanolSolvent

Procedure

The title compound was prepared by the method of Example 9 using 10.5 g of the product compound of Example 10, except that no hydrochloric acid was added during hydrogenation. The crude product was dissolved in methanol and acidified with HCl in isopropyl alcohol. Addition of diethyl ether induced precipitation of 11.6 g of the title compound. Structure assignment was supported by the nmr spectrum and by elemental analysis.

Workup

  1. additionwas added during hydrogenation
  2. customprecipitation of 11.6 g of the title compound

Sources & evidence

ORD record
ord-245c0e9667e74a76b9c591b84b6df39b
Source dataset
uspto-grants-1985_08
Patent number
US04533739

Reaction notes

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