Hydrazine hydrate (1:1) → HCID 19030658, compound

HRID 266680Notes

Reaction equation

HRID 266680 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]2[C:3]=1[C:4]([C:17]([O:19]CC)=O)=[C:5]([C:12](OCC)=[O:13])[NH:6]2.O.[NH2:23][NH2:24]>C(O)C>[Cl:11][C:9]1[CH:10]=[C:2]([Cl:1])[C:3]2[C:4]3[C:17](=[O:19])[N:24]=[N:23][C:12](=[O:13])[C:5]=3[NH:6][C:7]=2[CH:8]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 19030657HCID 19030657, compound

Product 1

HCID 19030658HCID 19030658, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of diethyl 4,6-dichloroindole-2,3-dicarboxylate (3.22 g, 9.8 mM) in ethanol (20 mL) was added hydrazine hydrate (14.2 mL, 294 mM). The solution was refluxed for 3 hours during which time a precipitate formed. The reaction mixture was then cooled to room temperature, the solid was filtered and heated to reflux in 3N HCl. After several minutes, the mixture was cooled to room temperature and the solid was filtered, washed with ethanol, and dried. This afforded the titled product as a white solid (2.6 g, 90%), mp >300° C. NMR (d6 -DMSO): 13.02 (br s, 1H), 11.72 (br s, 2H), 7.54 (s, 1H), 7.40 (s, 1H). MS(CI): 271(M+1).

Workup

  1. temperatureThe solution was refluxed for 3 hours during which time a precipitate
  2. customformed
  3. filtrationthe solid was filtered
  4. temperatureheated
  5. temperatureto reflux in 3N HCl
  6. waitAfter several minutes
  7. temperaturethe mixture was cooled to room temperature
  8. filtrationthe solid was filtered
  9. washwashed with ethanol
  10. customdried

Sources & evidence

ORD record
ord-78a2b4c795d742099b444bc6c3a792a8
Source dataset
uspto-grants-1997_07
Patent number
US05652239

Reaction notes

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