Hydrazine hydrate (1:1) → HCID 178462998, compound

HRID 597232Notes

Reaction equation

HRID 597232 reaction equation
Cl[C:2]1[C:7]2[CH:8]=[N:9][N:10]([CH2:11][CH3:12])[C:6]=2[N:5]=[C:4]2[CH2:13][CH2:14][C:15]3[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=3[C:17](=O)[C:3]=12.O.[NH2:24][NH2:25]>C(O)C>[CH2:11]([N:10]1[N:9]=[CH:8][C:7]2[C:2]3[NH:25][N:24]=[C:17]4[C:16]5[CH:19]=[CH:20][CH:21]=[CH:22][C:15]=5[CH2:14][CH2:13][C:4]([C:3]=34)=[N:5][C:6]1=2)[CH3:12]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 22758787HCID 22758787, compound

Product 1

HCID 178462998HCID 178462998, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 11.0 g. of 4-chloro-1-ethyl-10,11-dihydrobenzo[4,5]cyclohepta[1,2-b]pyrazolo[4,3-e]pyridin5(1H)one (0.035 mol.), 4.5 g. of hydrazine hydrate 98% (0.09 mol.) and 125 ml. of abs. ethanol is refluxed for 3 hours with stirring. Then the reaction solution is filtered while hot and allowed to crystallize in a refrigerator. The crystallized 2,5,7,8-tetrahydro-5-ethyl-1,2,4,5,6-pentaazabenzo[6,7]cyclohepta[1,2,3-cd]-as-indacene which is filtered off, washed with alcohol and ether, melts at 229°-231°. Evaporation of the mother liquor to dryness and treatment with water yields a further crop of 1.9 g. of the product. Total yield 97%. Recrystallization from ethanol elevates the melting point to 230°-232°.

Workup

  1. additionA mixture of 11.0 g
  2. filtrationThen the reaction solution is filtered while hot and
  3. customto crystallize in a refrigerator
  4. filtrationThe crystallized 2,5,7,8-tetrahydro-5-ethyl-1,2,4,5,6-pentaazabenzo[6,7]cyclohepta[1,2,3-cd]-as-indacene which is filtered off
  5. washwashed with alcohol and ether, melts at 229°-231°
  6. customEvaporation of the mother liquor to dryness and treatment with water
  7. customyields a further crop of 1.9 g
  8. customRecrystallization from ethanol elevates the melting point to 230°-232°

Sources & evidence

ORD record
ord-75eb154db5764226a72539b031914b8e
Source dataset
uspto-grants-1977_03
Patent number
US04013672

Reaction notes

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