Picolinohydrazide → HCID 23317235, compound

HRID 1982381Notes

Reaction equation

HRID 1982381 reaction equation
[Cl:1][C:2]1[C:8]2=CC=C[N:7]2[CH2:6][C:5]2[CH:12]=[CH:13][CH:14]=[CH:15][C:4]=2[N:3]=1.N1C=CC=CC=1C(NN)=O>C(O)C>[ClH:1].[NH:3]1[C:4]2[CH:15]=[CH:14][CH:13]=[CH:12][C:5]=2[CH:6]=[N:7][CH:8]=[CH:2]1

Participants

4

Reactant 2

HCID 255881PicolinohydrazideHCID 13649489HCID 13649489, compound

Product 1

HCID 23317235HCID 23317235, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Under an atmosphere of nitrogen, a slurry of 575 g of 11-chloro-5H-pyrrolo[2,1-c][1,4]benzodiazepine in 7.2 L of anhydrous ethanol is stirred while 364 g of pyridine-2-carboxylic acid hydrazide is added over a period of five minutes. The mixture is heated slowly to 65°. An exothermic reaction occurs and there is vigorous refluxing. When the refluxing subsides to a normal rate heating is continued and the mixture is stirred and refluxed for 21-22 hours. The product precipitates from the hot solution during the reflux period. The crystals are filtered off and washed on the filter with anhydrous ethanol. The product is air-dried overnight, then dried at high vacuum without heat for 2 days to yield 3-(2-pyridinyl)-9H-pyrrolo[2,1-c]-1,2,4-triazolo[4,3-a][1,4benzodiazepine hydrochloride, m.p. 265°-268° (d).

Workup

  1. additionis added over a period of five minutes
  2. temperatureThe mixture is heated slowly to 65°
  3. customAn exothermic reaction
  4. temperatureWhen the refluxing subsides to a normal rate heating
  5. temperaturerefluxed for 21-22 hours
  6. customThe product precipitates from the hot solution during the reflux period
  7. filtrationThe crystals are filtered off
  8. washwashed on the
  9. filtrationfilter with anhydrous ethanol
  10. customThe product is air-dried overnight
  11. customdried at high vacuum
  12. temperaturewithout heat for 2 days

Sources & evidence

ORD record
ord-7a617f7f2b3840f89cc3ed1484ec2b45
Source dataset
uspto-grants-1986_06
Patent number
US04596799

Reaction notes

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