N-methyl-2-pyrrolidone → HCID 20335566, compound

HRID 1706424Notes

Reaction equation

HRID 1706424 reaction equation
O.O.O.[Cl-:4].F[C:6]1[CH:15]=[CH:14][C:13]2[N+:12]3[CH:16]=[C:17]4[CH:26]=[CH:25][C:24]5[CH:23]=[C:22]([CH3:27])[CH:21]=[CH:20][C:19]=5[N:18]4[C:11]=3[CH:10]=[CH:9][C:8]=2[CH:7]=1.C[N:29]1[CH2:33][CH2:32][CH2:31][C:30]1=O.N1CCCC1>C(OCC)(=O)C>[Cl-:4].[CH3:27][C:22]1[CH:21]=[CH:20][C:19]2[N:18]3[C:11]4[CH:10]=[CH:9][C:8]5[CH:7]=[C:6]([N:29]6[CH2:33][CH2:32][CH2:31][CH2:30]6)[CH:15]=[CH:14][C:13]=5[N+:12]=4[CH:16]=[C:17]3[CH:26]=[CH:25][C:24]=2[CH:23]=1

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 31268PyrrolidineHCID 86737041HCID 86737041, compound

Product 1

HCID 20335566HCID 20335566, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A stirred mixture of 219.5 g. of 3-fluoro-10-methylimidazo[1,2-a:-3,4-a']diquinolin-15-ium chloride trihydrate and 580 ml. of N-methyl-2-pyrrolidinone is heated to 150° C. and 144 ml. of pyrrolidine is added over a 2 minute period. The mixture is heated and stirred at reflux (132°-140° C.) for 40 minutes, allowed to cool, and then is diluted with 2 l. of ethyl acetate. The precipitated solid is collected by filtration, washed with ethyl acetate, dried and dissolved in 1.6 l. of methanol. The methanol solution is treated with 20 g. of activated charcoal and filtered. The filtrate is passed over a column of 1 l. of IRA-410 anion exchange resin (Cl- form, suspended in methanol) over a period of 3 hours. The eluate is evaporated at reduced pressure to give a residue of 10-methyl-3-(1-pyrrolidinyl)-imidazo[1,2-a:3,4-a']diquinolin-15-ium chloride; m.p. 245°-320° C. (dec.) after crystallization from dimethylformamide and from 2-propanol/acetonitrile.

Workup

  1. additionA stirred mixture of 219.5 g
  2. temperatureThe mixture is heated
  3. temperatureat reflux (132°-140° C.) for 40 minutes
  4. temperatureto cool
  5. additionis diluted with 2 l
  6. filtrationThe precipitated solid is collected by filtration
  7. washwashed with ethyl acetate
  8. customdried
  9. dissolutiondissolved in 1.6 l
  10. additionThe methanol solution is treated with 20 g
  11. filtrationof activated charcoal and filtered
  12. customThe eluate is evaporated at reduced pressure

Sources & evidence

ORD record
ord-cf7bb9b7353d4c378aaedfcd5748d6d0
Source dataset
uspto-grants-1980_06
Patent number
US04207320

Reaction notes

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