Hydrazine hydrate (1:1) → HCID 2724959, compound

HRID 1692136Notes

Reaction equation

HRID 1692136 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[NH:11]C(OCC1C=CC=CC=1)=O.O.[NH2:24][NH2:25]>C(O)C>[NH2:11][C:5]1[CH:6]=[CH:7][C:8]([Cl:10])=[CH:9][C:4]=1[C:3]([NH:24][NH2:25])=[O:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 66905835HCID 66905835, compound

Product 1

HCID 2724959HCID 2724959, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-benzyloxycarbonylamino-5-chloro-benzoic acid methyl ester (3 g, 9.4 mmol) was dissolved in 30 mL ethanol. Hydrazine hydrate (1.5 mL, 30.0 mmol) was added and the resultant solution was heated at reflux under a nitrogen atmosphere for two hours, at which LCMS analysis showed complete conversion of the ester as well as the removal of the CBz protecting group. The reaction mixture was subsequently concentrated in vacuo to provide 1.6 g of 2-amino-5-chloro-benzoic acid hydrazide (light brown solid, 92% yield): HPLC retention time=2.21; MS (ES) M+H expected 186.0, found 186.0.

Workup

  1. temperatureat reflux under a nitrogen atmosphere for two hours, at which LCMS analysis
  2. customwell as the removal of the CBz protecting group
  3. concentrationThe reaction mixture was subsequently concentrated in vacuo

Sources & evidence

ORD record
ord-c503ee06c3324c69848c5cb7fb0c4d6b
Source dataset
uspto-grants-2012_04
Patent number
US08153818B2

Reaction notes

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