Hydrazine hydrate (1:1) → 2-Methoxy-2-(naphthalen-2-yl)acetohydrazide

HRID 388253Notes

Reaction equation

HRID 388253 reaction equation
[CH3:1][O:2][CH:3]([C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=1)[C:4](OC)=[O:5].O.[NH2:19][NH2:20]>>[CH3:1][O:2][CH:3]([C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=1)[C:4]([NH:19][NH2:20])=[O:5]

Participants

3

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 302866Methyl 2-methoxy-2-(naphthalen-2-yl)acetate

Product 1

HCID 591858932-Methoxy-2-(naphthalen-2-yl)acetohydrazideYield 47%

Procedure

A stirred solution of methyl 2-methoxy-2-(naphthalen-2-yl)acetate (0.358 g, 1 eq) and hydrazine hydrate (4 mL) was heated to reflux for 1 hour. The reaction mixture was then cooled and the solvents removed under reduced pressure. The crude oil was diluted with EtOAc and washed with H2O and the organic phase dried over Na2SO4, filtered, and the solvents removed under reduced pressure to yield a yellow oil (0.17 g, 47%) that was used without further purification.

Workup

  1. temperatureto reflux for 1 hour
  2. temperatureThe reaction mixture was then cooled
  3. customthe solvents removed under reduced pressure
  4. additionThe crude oil was diluted with EtOAc
  5. washwashed with H2O
  6. dry with materialthe organic phase dried over Na2SO4
  7. filtrationfiltered
  8. customthe solvents removed under reduced pressure

Sources & evidence

ORD record
ord-65ac9737f1d540dfbe5bac6e84ee52fe
Source dataset
uspto-grants-2013_02
Patent number
US08377930B2

Reaction notes

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