Hydrazine hydrate (1:1) → HCID 178526464, compound

HRID 2427835Notes

Reaction equation

HRID 2427835 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:5]=1F.O.[NH2:16][NH2:17]>C(O)C>[N+:10]([C:7]1[CH:6]=[C:5]2[C:4]([C:3]([OH:2])=[N:16][NH:17]2)=[CH:9][CH:8]=1)([O-:12])=[O:11]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)2×HCID 3013872Methyl 2-fluoro-4-nitrobenzoate

Product 1

HCID 178526464HCID 178526464, compoundYield 30.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Fluoro-4-nitrobenzoic acid methyl ester (5 g, 25.11 mmol) and hydrazine hydrate (1.34 ml, 27.62 mmol) were dissolved in 250 ml of ethanol and heated under reflux for 11 h. A further 0.26 ml of hydrazine hydrate were added and heated under reflux for a further 6 h, and the mixture was concentrated and ethyl acetate and water were added. The precipitated residue was filtered off with suction and dried. Purification by preparative HPLC (PR18, acetonitrile/water 0.1% TFA) resulted in 1.39 g of product, M+H+: 180.05.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 11 h
  3. temperatureheated
  4. temperatureunder reflux for a further 6 h
  5. concentrationthe mixture was concentrated
  6. additionethyl acetate and water were added
  7. filtrationThe precipitated residue was filtered off with suction
  8. customdried
  9. customPurification by preparative HPLC (PR18, acetonitrile/water 0.1% TFA)

Sources & evidence

ORD record
ord-f249a6610f554290bc5c05a95dba2848
Source dataset
uspto-grants-2011_06
Patent number
US07968719B2

Reaction notes

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