Isatoic Anhydride → 2-amino-benzoic acid N'-pyridin-2-yl-hydrazide

HRID 30404

Reaction equation

HRID 30404 reaction equation
[C:1]12[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH:6]C(=O)[O:4][C:2]2=O.[NH:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)[NH2:14]>CCO>[N:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[NH:13][NH:14][C:2](=[O:4])[C:1]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[NH2:6]

Participants

4

Reactant 2

HCID 8359Isatoic AnhydrideHCID 786452-Hydrazinopyridine

Product 1

HCID 685335622-amino-benzoic acid N'-pyridin-2-yl-hydrazideYield 546.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of isatoic anhydride (3.51 g, 2.15 mmol) and 2-hydrazinopyridine (2.40 g, 2.20 mmol) in 35 ml of EtOH was refluxed for 17 hours. After refluxing for 15 minutes, the suspension turned into a brown solution and gas evolution was observed. At the end of the 17 hour period, the reaction mixture was cooled to room temperature and the brown solution was concentrated on a rotary evaporator. The residue was chromatographed on silica gel with 65% EtOAc in hexanes. The fractions containing the product were collected and concentrated. The solid was triturated with ether (100 ml) for 15 minutes and collected by filtration. It was air-dried to give 2.68 g of 2-amino-benzoic acid N′-pyridin-2-yl-hydrazide (Intermediate 9) as a white solid. MS (APCI): 229 (M+1, 100%).

Workup

  1. temperaturewas refluxed for 17 hours
  2. temperatureAfter refluxing for 15 minutes
  3. concentrationthe brown solution was concentrated on a rotary evaporator
  4. customThe residue was chromatographed on silica gel with 65% EtOAc in hexanes
  5. additionThe fractions containing the product
  6. customwere collected
  7. concentrationconcentrated
  8. customThe solid was triturated with ether (100 ml) for 15 minutes
  9. filtrationcollected by filtration
  10. customIt was air-dried

Sources & evidence

ORD record
ord-8628a3cc9ef94a3f9cd200bd63018a30
Source dataset
uspto-grants-2008_09
Patent number
US07423054B2

Linked notes

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