Hydrazine hydrate (1:1) → HCID 178469891, compound

HRID 456632Notes

Reaction equation

HRID 456632 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]([C:13]2[C:14](Cl)=[N:15][CH:16]=[CH:17][CH:18]=2)=O)[NH:8][CH:7]=1)=[O:5])[CH3:2].O.[NH2:21][NH2:22]>C(O)C>[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]2[C:13]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[NH:22][N:21]=2)[NH:8][CH:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86592241ethyl 5-(2-chloronicotinoyl)-1H-pyrrole-3-carboxylate

Product 1

HCID 178469891HCID 178469891, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-(2-chloro-pyridine-3-carbonyl)-1H-pyrrole-3-carboxylic acid ethyl ester (1.2 g, 4.32 mmol) and hydrazine hydrate (6.27 mL) in ethanol (50 mL) was heated at 80° C. for 24 hours. The reaction was concentrated and the residue was neutralized to pH 7 with 1N HCl, extracted with ethyl acetate. The combined ethyl acetate was dried, concentrated and purified on a silica gel column to give the titled compound as a white solid.

Workup

  1. concentrationThe reaction was concentrated
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined ethyl acetate was dried
  4. concentrationconcentrated
  5. custompurified on a silica gel column

Sources & evidence

ORD record
ord-cf11c95bd4e749a0aaf8dee585cee705
Source dataset
uspto-grants-2007_03
Patent number
US07186716B2

Reaction notes

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