Sodium Hydroxide → 2-Hydroxy-3-nitrobenzenecarbohydrazide

HRID 1281659Notes

Reaction equation

HRID 1281659 reaction equation
O.[NH2:2][NH2:3].[N+:4]([C:7]1[CH:16]=[CH:15][CH:14]=[C:9]([C:10](OC)=[O:11])[C:8]=1[OH:17])([O-:6])=[O:5].[OH-].[Na+]>O1CCCC1>[OH:17][C:8]1[C:7]([N+:4]([O-:6])=[O:5])=[CH:16][CH:15]=[CH:14][C:9]=1[C:10]([NH:2][NH2:3])=[O:11]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 596904Methyl 2-hydroxy-3-nitrobenzoate

Product 1

HCID 113676062-Hydroxy-3-nitrobenzenecarbohydrazideYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

40 ml of hydrazine hydrate were added to a solution of 30 g (0.15 mol) of methyl 3-nitrosalicylate in 200 ml of anhydrous tetrahydrofuran (THF). After dilution with THF, the resulting suspension was stirrable; it was refluxed for approximately 18 hours. After cooling, the batch was poured onto ice. The aqueous solution was rendered neutral by adding NaOH solution. The crystals which precipitated were filtered off and washed with water. After drying, 27 g (90%) of the title compound were obtained.

Workup

  1. temperatureit was refluxed for approximately 18 hours
  2. temperatureAfter cooling
  3. additionthe batch was poured onto ice
  4. customThe crystals which precipitated
  5. filtrationwere filtered off
  6. washwashed with water
  7. customAfter drying

Sources & evidence

ORD record
ord-be80d6a2740b47469a8435481c37587a
Source dataset
uspto-grants-2002_09
Patent number
US06455515B2

Reaction notes

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