Hydrazine → 4-Amino-3-nitrobenzohydrazide

HRID 1513271Notes

Reaction equation

HRID 1513271 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].C(N=C=NC(C)C)(C)C.[NH2:23][NH2:24]>C1COCC1>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:23][NH2:24])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 9321HydrazineHCID 12734DiisopropylcarbodiimideHCID 74115Benzoic acid, 4-amino-3-nitro-

Product 1

HCID 247214084-Amino-3-nitrobenzohydrazide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 4-amino-3-nitrobenzoic acid (1.64 g, 9 mmol) in THF (25 mL) was added diisopropylcarbodiimide (1.13 g, 9 mmol). The mixture was stirred at RT for 15 min and to the resulting yellow solution was added hydrazine (600 mg, 18 mmol). The resulting orange suspension was stirred at RT for 2 h. The solid was filtered and washed twice with THF to give the title compound: MS: m/z 195.1 (M−1).

Workup

  1. stirringThe resulting orange suspension was stirred at RT for 2 h
  2. filtrationThe solid was filtered
  3. washwashed twice with THF

Sources & evidence

ORD record
ord-3b42b1ba81e64ad799942aa4a25b150f
Source dataset
uspto-grants-2012_07
Patent number
US08217065B2

Reaction notes

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