Hydrazine hydrate (1:1) → 2-Fluoro-4-methoxybenzohydrazide

HRID 1809415Notes

Reaction equation

HRID 1809415 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:5]=1[F:12].O.[NH2:15][NH2:16]>C(O)C>[F:12][C:5]1[CH:6]=[C:7]([O:10][CH3:11])[CH:8]=[CH:9][C:4]=1[C:3]([NH:15][NH2:16])=[O:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 21255685Methyl 2-fluoro-4-methoxybenzoate

Product 1

HCID 157020782-Fluoro-4-methoxybenzohydrazideYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5.04 g (27.2 mmol) of 2-fluoro-4-methoxybenzoic acid methyl ester in ethanol (50 mL) are added 36.9 mL (408.6 mmol) of hydrazine hydrate. The reaction is stirred at room temperature for 15 h. The mixture is concentrated under reduced pressure and the solid is washed with DCM/heptane (2:1) to give 4.26 g (23.0 mmol) of 2-fluoro-4-methoxybenzoic acid hydrazide. Yield: 85%, ES-MS: m/z [M+H] 185.

Workup

  1. concentrationThe mixture is concentrated under reduced pressure
  2. washthe solid is washed with DCM/heptane (2:1)

Sources & evidence

ORD record
ord-98c5f1e5ed444375b476a162ddbd4136
Source dataset
uspto-grants-2013_01
Patent number
US08362039B2

Reaction notes

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