Hydrazine hydrate (1:1) → HCID 19030660, compound

HRID 266682Notes

Reaction equation

HRID 266682 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:16]([O:18]CC)=O)=[C:7]([C:11](OCC)=[O:12])[NH:8]2)=[CH:4][CH:3]=1.O.[NH2:22][NH2:23]>C(O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:16](=[O:18])[N:23]=[N:22][C:11](=[O:12])[C:7]=3[NH:8][C:9]=2[CH:10]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 19030628HCID 19030628, compound

Product 1

HCID 19030660HCID 19030660, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of diethyl 6-bromoindole-2,3-dicarboxylate (0.5 g, 1.47 mM) in ethanol (4 mL) was added hydrazine hydrate (2.2 mL, 44 mM). The solution was heated to reflux for 90 minutes and then cooled to room temperature. The resulting solid was filtered and then suspended in glacial acetic acid (5 mL). After heating this mixture to reflux for several minutes and cooling to room temperature, the solid was filtered off and dried under vacuum. This afforded the titled compound as a white solid (0.35 g, 85%), mp 260° C. NMR (d6 -DMSO): 11.81 (br s, 2H), 8.04 (dd, J1 =1.0 Hz, J2 =8 Hz), 7.76 (s, 1H), 7.46 (d, J=8 Hz), 3.36 (br s, 1H). MS(CI): 280 (M+1).

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 90 minutes
  3. filtrationThe resulting solid was filtered
  4. temperatureAfter heating this mixture
  5. temperatureto reflux for several minutes
  6. temperaturecooling to room temperature
  7. filtrationthe solid was filtered off
  8. customdried under vacuum

Sources & evidence

ORD record
ord-c8eb7e7a519e4d90867159fc85879c62
Source dataset
uspto-grants-1997_07
Patent number
US05652239

Reaction notes

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