N-methyl-2-pyrrolidone → HCID 20335540, compound

HRID 1706431Notes

Reaction equation

HRID 1706431 reaction equation
[I-:1].Cl[C:3]1[CH:12]=[CH:11][C:10]2[N+:9]3[CH:13]=[C:14]4[CH:23]=[CH:22][C:21]5[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=5[N:15]4[C:8]=3[CH:7]=[CH:6][C:5]=2[CH:4]=1.[NH:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1.CN1CCCC1=O>C(OCC)(=O)C>[I-:1].[N:24]1([C:3]2[CH:12]=[CH:11][C:10]3[N+:9]4[CH:13]=[C:14]5[CH:23]=[CH:22][C:21]6[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=6[N:15]5[C:8]=4[CH:7]=[CH:6][C:5]=3[CH:4]=2)[CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 31268PyrrolidineHCID 20335580HCID 20335580, compound

Product 1

HCID 20335540HCID 20335540, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1.0 g. of 3-chloroimidazo[1,2-a:3,4-a']diquinolin-15-ium iodide, 1.0 ml. of pyrrolidine and 5 ml. of N-methyl-2-pyrrolidinone is stirred and heated at reflux for 17 hours, cooled and diluted with 100 ml. of ethyl acetate. The precipitate of 3-(1-pyrrolidinyl)imidazo[1,2-a:3,4-a']diquinolin-15-ium iodide is collected by filtration, stirred with 50 ml. of 1% aqueous triethylamine hydroiodide and recollected; m.p. 312°-320° C. after crystallization from methanol.

Workup

  1. additionA mixture of 1.0 g
  2. temperatureheated
  3. temperatureat reflux for 17 hours
  4. temperaturecooled
  5. additiondiluted with 100 ml
  6. filtrationThe precipitate of 3-(1-pyrrolidinyl)imidazo[1,2-a:3,4-a']diquinolin-15-ium iodide is collected by filtration
  7. customm.p. 312°-320° C. after crystallization from methanol

Sources & evidence

ORD record
ord-5029a163b70e43769144f5650785c381
Source dataset
uspto-grants-1980_06
Patent number
US04207320

Reaction notes

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