1,1-Dimethylhydrazine → HCID 20335514, compound

HRID 1706433Notes

Reaction equation

HRID 1706433 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].[CH3:28][N:29]([CH3:31])[NH2:30].CN1CCCC1=O>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]([NH:30][N:29]([CH3:31])[CH3:28])[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 59761,1-DimethylhydrazineHCID 13387N-methyl-2-pyrrolidoneHCID 20335571HCID 20335571, compound

Product 1

HCID 20335514HCID 20335514, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1.46 g. of 10-(1,1-dimethylethyl)-3-fluoroimidazo-[1,2-a:3,4-a']diquinolin-15-ium iodide, 1.64 ml. of 1,1-dimethylhydrazine and 25 ml. of N-methyl-2-pyrrolidinone is heated at reflux for 15 hours, then cooled and diluted with 300 ml. of ethyl acetate. The precipitate is collected and stirred with 1% aqueous triethylamine hydroiodide. The solid is collected, washed with water and dissolved in 150 ml. of hot methanol. The methanol solution is treated with activated charcoal, filtered, evaporated to a volume of about 25 ml. and cooled. The resulting precipitate of 10-(1,1-dimethylethyl)-3-(2,2-dimethylhydrazino)imidazo[1,2-a:3,4-a']diquinolin-15-ium iodide is collected by filtration, washed with cold methanol and dried; m.p. 347°-350° C., after two crystallizations from 2-propanol/ethanol.

Workup

  1. additionA mixture of 1.46 g
  2. temperatureat reflux for 15 hours
  3. temperaturecooled
  4. additiondiluted with 300 ml
  5. customThe precipitate is collected
  6. customThe solid is collected
  7. washwashed with water
  8. dissolutiondissolved in 150 ml
  9. additionThe methanol solution is treated with activated charcoal
  10. filtrationfiltered
  11. customevaporated to a volume of about 25 ml
  12. temperatureand cooled
  13. filtrationThe resulting precipitate of 10-(1,1-dimethylethyl)-3-(2,2-dimethylhydrazino)imidazo[1,2-a:3,4-a']diquinolin-15-ium iodide is collected by filtration
  14. washwashed with cold methanol
  15. customdried
  16. customm.p. 347°-350° C., after two crystallizations from 2-propanol/ethanol

Sources & evidence

ORD record
ord-e218da6cd1e14a9291a1e16c5bebb4e3
Source dataset
uspto-grants-1980_06
Patent number
US04207320

Reaction notes

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