Hydrazine hydrate (1:1) → HCID 19030652, compound

HRID 266685Notes

Reaction equation

HRID 266685 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[Cl:12])[NH:8][C:7]([C:13](OC)=[O:14])=[C:6]2[C:17]([O:19]C)=O.O.[NH2:22][NH2:23]>C(O)C>[Cl:12][C:11]1[C:3]([O:2][CH3:1])=[CH:4][C:5]2[C:6]3[C:17](=[O:19])[N:23]=[N:22][C:13](=[O:14])[C:7]=3[NH:8][C:9]=2[CH:10]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 19030648HCID 19030648, compound

Product 1

HCID 19030652HCID 19030652, compoundYield 30.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethanol (15 ml) and dimethyl 5-methoxy-6-chloroindole-2,3-dicarboxylate (0.67 g, 2.30 mM), was added hydrazine hydrate (3.45 g, 0.69 mM). The resulting heterogeneous mixture was refluxed for 5 hr and then cooled to room temperature. The ethanol was removed under reduced pressure, acetic acid (15 ml) was added, and the resulting mixture refluxed for 2 hr. The reaction was cooled to room temperature, filtered, and dried. This afforded the titled compound as a white solid (0.18 g, 30%).

Workup

  1. temperatureThe resulting heterogeneous mixture was refluxed for 5 hr
  2. customThe ethanol was removed under reduced pressure, acetic acid (15 ml)
  3. additionwas added
  4. temperaturethe resulting mixture refluxed for 2 hr
  5. temperatureThe reaction was cooled to room temperature
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-e3fe20c18b474602a58b322002892c74
Source dataset
uspto-grants-1997_07
Patent number
US05652239

Reaction notes

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