Hydrazine hydrate (1:1) → HCID 59185885, compound

HRID 388265Notes

Reaction equation

HRID 388265 reaction equation
[CH3:1][N:2]([CH3:17])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]([O:15][CH3:16])[C:10](OCC)=[O:11])=[CH:5][CH:4]=1.O.[NH2:19][NH2:20]>C(O)C>[CH3:1][N:2]([CH3:17])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]([O:15][CH3:16])[C:10]([NH:19][NH2:20])=[O:11])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)2×HCID 59185864HCID 59185864, compound

Product 1

HCID 59185885HCID 59185885, compoundYield 38.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 2-(4-(dimethylamino)phenyl)-2-methoxyacetate (0.675 g, 2.84 mmol) in absolute ethanol (20 mL) was added hydrazine hydrate (0.8 mL, 16.4 mmol) and the mixture was heated at reflux for 22 hours. Additional hydrazine hydrate (1.0 mL, 20.6 mmol) was added and the heating continued for 7 hours. After cooling to room temperature, the mixture was concentrated in vacuo. The residue was dissolved in EtOAc and washed with water and brine, dried over Na2SO4 and concentrated in vacuo. The solid product was stirred with hot diethyl ether then hexanes were added. After cooling to room temperature, the solids were collected on a Büchner funnel and rinsed with 50% diethyl ether-hexanes then dried under vacuum to give 2-(4-(dimethylamino)phenyl)-2-methoxyacetohydrazide as an orange solid (0.246 g). Additional product was isolated from the mother liquor by chromatography (80-100% EtOAc-hexanes, then 5% methanol-EtOAc) to give an off-white solid (0.173 g, 66% yield total).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 22 hours
  3. concentrationthe mixture was concentrated in vacuo
  4. dissolutionThe residue was dissolved in EtOAc
  5. washwashed with water and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. additionhexanes were added
  9. temperatureAfter cooling to room temperature
  10. customthe solids were collected on a Büchner funnel
  11. washrinsed with 50% diethyl ether-hexanes
  12. customthen dried under vacuum

Sources & evidence

ORD record
ord-372d3270dba74e39aa9f88a886192219
Source dataset
uspto-grants-2013_02
Patent number
US08377930B2

Reaction notes

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