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

HRID 1802412Notes

Reaction equation

HRID 1802412 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-ee10fae7e7b348b1b4b6be2b97be065d
Source dataset
uspto-grants-2013_01
Patent number
US08349871B2

Reaction notes

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