4-Aminopyridine → HCID 15521669, compound

HRID 2303387Notes

Reaction equation

HRID 2303387 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=[O:3].[N+:7]([C:10]1[CH:25]=[CH:24][C:13]([CH2:14][N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[CH:16]2)=[CH:12][CH:11]=1)([O-:9])=[O:8].[NH2:26][C:27]1[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=1>CCOCC.O1CCCC1>[N:30]1[CH:31]=[CH:32][C:27]([NH:26][C:1](=[O:5])[C:2]([C:17]2[C:18]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:15]([CH2:14][C:13]3[CH:12]=[CH:11][C:10]([N+:7]([O-:9])=[O:8])=[CH:25][CH:24]=3)[CH:16]=2)=[O:3])=[CH:28][CH:29]=1

Participants

6

Reactant 3

HCID 17274-AminopyridineHCID 65578Oxalyl chlorideHCID 42892251-[(4-Nitrophenyl)methyl]-1H-indole

Product 1

HCID 15521669HCID 15521669, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-5 °C

Procedure

A solution of 4.50 ml of oxalyl chloride in 50 ml of ether is treated dropwise with a solution of 10.09 g (0.04 mol) of 1-(4-nitrobenzyl)indole in 50 ml of ether at OC [sic] and under a nitrogen atmosphere. The mixture is heated at reflux temperature for 2 hours and the solvent is then evaporated. 100 ml of tetrahydrofuran are added to the residue, it is cooled to −5° C. and a solution of of [sic] 9.32 g (0.099 mol) of 4-aminopyridine in 400 ml of tetrahydrofuran is added dropwise. The mixture is heated to reflux for 3 hours and allowed to stand at room temperature overnight. The 4-aminopyridine hydrochloride is filtered off with suction, the precipitate is washed with tetrahydrofuran, the filtrate is concentrated in vacuo and the residue is recrystallized from ethyl acetate.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux temperature for 2 hours
  3. customthe solvent is then evaporated
  4. addition100 ml of tetrahydrofuran are added to the residue, it
  5. temperatureThe mixture is heated
  6. temperatureto reflux for 3 hours
  7. filtrationThe 4-aminopyridine hydrochloride is filtered off with suction
  8. washthe precipitate is washed with tetrahydrofuran
  9. concentrationthe filtrate is concentrated in vacuo
  10. customthe residue is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-16d07ce07eda4bc098a3b8d54a458e59
Source dataset
uspto-grants-2002_08
Patent number
US06432987B1

Reaction notes

Loading…