N-methyl-2-pyrrolidone → HCID 20335555, compound

HRID 1706428Notes

Reaction equation

HRID 1706428 reaction equation
[I-:1].[CH3:2][C:3]([C:6]1[CH:15]=[CH:14][C:13]2[N:12]3[C:16]4[CH:25]=[CH:24][C:23]5[CH:22]=[C:21](F)[CH:20]=[CH:19][C:18]=5[N+:17]=4[CH:27]=[C:11]3[CH:10]=[CH:9][C:8]=2[CH:7]=1)([CH3:5])[CH3:4].C[N:29]1[CH2:33][CH2:32][CH2:31][C:30]1=O.N1CCCC1>C(OCC)(=O)C>[I-:1].[CH3:2][C:3]([C:6]1[CH:15]=[CH:14][C:13]2[N:12]3[C:16]4[CH:25]=[CH:24][C:23]5[CH:22]=[C:21]([N:29]6[CH2:33][CH2:32][CH2:31][CH2:30]6)[CH:20]=[CH:19][C:18]=5[N+:17]=4[CH:27]=[C:11]3[CH:10]=[CH:9][C:8]=2[CH:7]=1)([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 31268PyrrolidineHCID 20335571HCID 20335571, compound

Product 1

HCID 20335555HCID 20335555, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 141 g. of 10-(1,1-dimethylethyl)-3-fluoroimidazo[1,2-a:3,4-a']diquinolin-15-ium iodide, 725 ml. of N-methyl-2-pyrrolidinone and 75 ml. of pyrrolidine is stirred and heated at reflux for 1 hour, then cooled and diluted with 3.6 l. of ethyl acetate. The resulting precipitate of 10-(1,1-dimethylethyl)-3-(1-pyrrolidinyl)imidazo[1,2-a:3,4-a']diquinolin-15-ium iodide is collected by filtration, washed with water and dried; m.p. >360° C.

Workup

  1. additionA mixture of 141 g
  2. temperatureheated
  3. temperatureat reflux for 1 hour
  4. temperaturecooled
  5. additiondiluted with 3.6 l
  6. filtrationThe resulting precipitate of 10-(1,1-dimethylethyl)-3-(1-pyrrolidinyl)imidazo[1,2-a:3,4-a']diquinolin-15-ium iodide is collected by filtration
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-68170bdff34641b8a79a61929aa6e060
Source dataset
uspto-grants-1980_06
Patent number
US04207320

Reaction notes

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