Hydrazine hydrate (1:1) → 3-Bromo-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carboxylic acid hydrazide

HRID 1506029Notes

Reaction equation

HRID 1506029 reaction equation
C[O:2][C:3]([C:5]1[N:13]=[CH:12][C:11]2[NH:10][C:9]3[N:14]=[CH:15][C:16]([Br:18])=[CH:17][C:8]=3[C:7]=2[CH:6]=1)=O.O.[NH2:20][NH2:21]>C(O)C>[Br:18][C:16]1[CH:15]=[N:14][C:9]2[NH:10][C:11]3[CH:12]=[N:13][C:5]([C:3]([NH:20][NH2:21])=[O:2])=[CH:6][C:7]=3[C:8]=2[CH:17]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 58266719Methyl 3-bromo-9H-pyrrolo[2,3-b:5,4-c']dipyridine-6-carboxylate

Product 1

HCID 582668173-Bromo-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carboxylic acid hydrazide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-bromo-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carboxylic acid methyl ester (582 mg, 1.90 mmol) and hydrazine hydrate (2.29 mL, 47.0 mmol) in ethanol (4.6 mL) was heated under reflux in an inert atmosphere. After 1 h, the reaction mixture was allowed to cool to ambient temperature. The resultant precipitate was collected by filtration, washed with ethanol, and left to air-dry to afford the title compound as a tan-yellow solid.

Workup

  1. temperatureunder reflux in an inert atmosphere
  2. filtrationThe resultant precipitate was collected by filtration
  3. washwashed with ethanol
  4. waitleft
  5. customto air-dry

Sources & evidence

ORD record
ord-b91ee7238fa2432db6ae6efa568e9ebb
Source dataset
uspto-grants-2015_12
Patent number
US09216980B2

Reaction notes

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