Hydrochloric Acid → HCID 19016524, compound

HRID 1728605Notes

Reaction equation

HRID 1728605 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[CH3:11].[N:12]1[CH:17]=[CH:16][CH:15]=[C:14]([N:18]=[C:19]=[O:20])[CH:13]=1.[ClH:21]>ClCCl.C(O)C>[ClH:21].[CH3:11][N:6]1[C:7]2[C:3](=[C:2]([NH:1][C:19]([NH:18][C:14]3[CH:13]=[N:12][CH:17]=[CH:16][CH:15]=3)=[O:20])[CH:10]=[CH:9][CH:8]=2)[CH:4]=[CH:5]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 27604933-IsocyanatopyridineHCID 221703071-methyl-1H-indol-4-amine

Product 1

HCID 19016524HCID 19016524, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of the aminoindole (D10) (0.44 g; 3.01 mM) in dichloromethane (10 ml) was added dropwise to a solution of 3-pyridyl isocyanate (D4) (prepared from 3-pyridine carbonyl azide (0.51 g; 3.4 mM) in toluene) at room temperature. The reaction mixture was stirred for 17 h, then cooled and the precipitate filtered off to give the crude product (1 g; 100%). This was dissolved in hot ethanol and ethereal hydrogen chloride added to afford the title compound as its hydrochloride salt (0.74 g; 81%), m.p 238° C.

Workup

  1. temperaturecooled
  2. filtrationthe precipitate filtered off
  3. customto give the crude product (1 g; 100%)

Sources & evidence

ORD record
ord-625c119a8f614b5a9a67033e7699d135
Source dataset
uspto-grants-1994_07
Patent number
US05328922

Reaction notes

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