Hydrazine hydrate (1:1) → HCID 19030662, compound

HRID 266683Notes

Reaction equation

HRID 266683 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([C:16]([O:18]CC)=O)=[C:5]([C:11](OCC)=[O:12])[NH:6]2.O.[NH2:22][NH2:23]>C(O)C>[Br:1][C:2]1[C:3]2[C:4]3[C:16](=[O:18])[N:23]=[N:22][C:11](=[O:12])[C:5]=3[NH:6][C:7]=2[CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 19030637HCID 19030637, compound

Product 1

HCID 19030662HCID 19030662, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of diethyl 4-bromoindole-2,3-dicarboxylate (0.4 g, 1.2 mM) in ethanol (3 mL) was added hydrazine hydrate (2.0 mL, 40 mM). The mixture was heated to reflux for 2 hours, cooled to room temperature, and the resulting solid was filtered. This was then suspended in glacial acetic acid (3 mL), heated to reflux for several minutes, and cooled to room temperature. The solid was then filtered and dried. This afforded the titled compound as a white solid (0.3 g, 88%), mp >260° C. NMR (d6 -DMSO): 12.8 (br s, 1H), 11.52 (br s, 2H), 7.60 (d, J=8 Hz, 1H), 7.52 (d, J=8 Hz, 1H), 7.52 (d, J=8 Hz, 1H), 7.32 (t, J=8 Hz, 1H). MS(CI): 280(M+1).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 hours
  3. filtrationthe resulting solid was filtered
  4. temperatureheated
  5. temperatureto reflux for several minutes
  6. temperaturecooled to room temperature
  7. filtrationThe solid was then filtered
  8. customdried

Sources & evidence

ORD record
ord-4083adcc53d54005a9e601a164cc90d7
Source dataset
uspto-grants-1997_07
Patent number
US05652239

Reaction notes

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