Hydrazine hydrate (1:1) → HCID 67267334, compound

HRID 598133Notes

Reaction equation

HRID 598133 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]1[CH:13]=[CH:12][C:11]([C:14](OCC)=[O:15])=[C:10]1[C:19]([O:21]CC)=O.O.[NH2:25][NH2:26]>C(O)C>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:10]2[C:19](=[O:21])[NH:25][NH:26][C:14](=[O:15])[C:11]=2[CH:12]=[CH:13]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)2×HCID 67266990HCID 67266990, compound

Product 1

HCID 67267334HCID 67267334, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of diethyl 1-(2,4-dimethylphenyl)-1H-pyrrole-2,3-dicarboxylate (0.5 g, 1.59 mmol) in ethanol (5 ml) was added hydrazine monohydrate (0.38 ml, 7.93 mmol) and the mixture was heated under reflux for 14 hours. During the reaction, additional hydrazine monohydrate (0.2 ml×3) was added to the mixture. The solvent was removed in vacuo and the residue was treated with 2N hydrochloric acid at 80° C. for 20 min. After cooling, crystals were collected by filtration, washed with water and dried to give 0.36 g (89%) of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 14 hours
  3. additionwas added to the mixture
  4. customThe solvent was removed in vacuo
  5. additionthe residue was treated with 2N hydrochloric acid at 80° C. for 20 min
  6. temperatureAfter cooling
  7. filtrationcrystals were collected by filtration
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-8a421f9daf514e2aa4295825df5c3435
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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