Hydrazine hydrate (1:1) → HCID 178518895, compound

HRID 469520Notes

Reaction equation

HRID 469520 reaction equation
[C:1]([C:9]1[C:10]([C:15]([OH:17])=O)=[N:11][CH:12]=[CH:13][CH:14]=1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[NH2:19][NH2:20]>CCO>[C:2]1([C:1]2[N:20]=[N:19][C:15]([OH:17])=[C:10]3[N:11]=[CH:12][CH:13]=[CH:14][C:9]=23)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 7269413-Benzoylpicolinic acid

Product 1

HCID 178518895HCID 178518895, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-benzoylpicolinic acid (0.272 g, 0.120 mmol) and hydrazine hydrate (0.17 mL, 0.37 mmol) in EtOH (3.3 mL) was stirred at 80° C. overnight, concentrated, diluted with saturated aqueous NaHCO3, extracted with CH2Cl2, dried (Na2SO4), and concentrated to give the title compound as a white solid (0.28 g, 0.12 mmol). 1H NMR (300 MHz, DMSO-d6) δ 13.09 (s, 1H), 9.10 (dd, 1H), 8.09 (dd, 1H), 7.88 (dd, 1H), 7.54-7.63 (m, 5H).

Workup

  1. concentrationconcentrated
  2. additiondiluted with saturated aqueous NaHCO3
  3. extractionextracted with CH2Cl2
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1b449b8e9a694b3ebea56a1ea5f55bf0
Source dataset
uspto-grants-2014_01
Patent number
US08629143B2

Reaction notes

Loading…