Hydrazine hydrate (1:1) → 2-(4-Cyanophenoxy)acetic acid hydrazide

HRID 642141Notes

Reaction equation

HRID 642141 reaction equation
[C:1]([C:3]1[CH:14]=[CH:13][C:6]([O:7][CH2:8][C:9](OC)=[O:10])=[CH:5][CH:4]=1)#[N:2].O.[NH2:16][NH2:17]>>[C:1]([C:3]1[CH:14]=[CH:13][C:6]([O:7][CH2:8][C:9]([NH:16][NH2:17])=[O:10])=[CH:5][CH:4]=1)#[N:2]

Participants

3

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 1506457methyl (4-cyanophenoxy)acetate

Product 1

HCID 23850492-(4-Cyanophenoxy)acetic acid hydrazideYield 75%

Procedure

To a solution of methyl (4-cyanophenoxy)acetate (3.52 g, 18.4 mmol) in MEOH (100 mL) was added hydrazine hydrate (8.9 mL). After stirring for 1 h at rt, a solid precipitated out. Filtration, washing with MeOH (5 mL) and water (4×10 mL) and drying under vacuo at 50° C. overnight gave the title compound (2.63 g, 75%) as a white solid in 98.4% purity by HPLC (MaxPlot detection between 230 and 400 nm).

Workup

  1. customa solid precipitated out
  2. filtrationFiltration
  3. washwashing with MeOH (5 mL) and water (4×10 mL)
  4. customdrying under vacuo at 50° C. overnight

Sources & evidence

ORD record
ord-26d65b9c08db480d8599ba26a9c04fba
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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