Hydrazine hydrate (1:1) → HCID 59185914, compound

HRID 388255Notes

Reaction equation

HRID 388255 reaction equation
[O:1]1[CH2:6][CH2:5][O:4][C:3]2[CH:7]=[C:8]([CH:11]([O:16][CH3:17])[C:12](OC)=[O:13])[CH:9]=[CH:10][C:2]1=2.O.[NH2:19][NH2:20]>CCO>[O:1]1[CH2:6][CH2:5][O:4][C:3]2[CH:7]=[C:8]([CH:11]([O:16][CH3:17])[C:12]([NH:19][NH2:20])=[O:13])[CH:9]=[CH:10][C:2]1=2

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 59185904HCID 59185904, compound

Product 1

HCID 59185914HCID 59185914, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred solution of methyl 2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-methoxyacetate (18.3 mmol) in anhydrous EtOH (150 mL) was added hydrazine hydrate (73.2 mmol, 4 eq) and heated to 90° C. Stirring was then continued for 24 hours. 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 (3.5 g) that was used without further purification.

Workup

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

Sources & evidence

ORD record
ord-a347ff79ab8d49309861d06b8adcb6c4
Source dataset
uspto-grants-2013_02
Patent number
US08377930B2

Reaction notes

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