Hydrazine hydrate (1:1) → HCID 19030664, compound

HRID 266678Notes

Reaction equation

HRID 266678 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11](OCC)=[O:12])=[C:7]2[C:16]([O:18]CC)=O.O.[NH2:22][NH2:23]>C(O)C>[Cl:1][C:2]1[C:10]2[NH:9][C:8]3[C:11](=[O:12])[N:22]=[N:23][C:16](=[O:18])[C:7]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 19030640HCID 19030640, compound

Product 1

HCID 19030664HCID 19030664, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of diethyl 7-chloroindole-2,3-dicarboxylate (0.6 g, 2.0 mM) in ethanol (4 mL) was added hydrazine hydrate (2 mL, 40 mM). The resulting solution was heated to reflux for 3 hrs during which time a white precipitate formed. The solid was filtered, suspended in acetic acid (2 mL), and warmed to reflux for several minutes. The mixture was then cooled to room temperature and the solid filtered and dried. This provided the titled compound as a white solid (0.11 g, 23%), mp >250° C. NMR (d6 -DMSO): 12.92 (s, 1H), 11.66 (s, 2H), 8.08 (d, J=8 Hz, 1H), 7.56 (d, J=8 Hz), 7.32 (t, J=8 Hz). MS(CI): 236(M+1).

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux for 3 hrs during which time a white precipitate
  3. customformed
  4. filtrationThe solid was filtered
  5. temperaturewarmed
  6. temperatureto reflux for several minutes
  7. filtrationthe solid filtered
  8. customdried

Sources & evidence

ORD record
ord-a20ef38430bf40a2ac80bf288487eae8
Source dataset
uspto-grants-1997_07
Patent number
US05652239

Reaction notes

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