Hydrazine hydrate (1:1) → HCID 53328542, compound

HRID 1190874Notes

Reaction equation

HRID 1190874 reaction equation
O.NN.[Br:4][C:5]1[C:10]([CH3:11])=[CH:9][C:8]([N+:12]([O-:14])=[O:13])=[CH:7][C:6]=1[CH2:15][N:16]1C(=O)C2C(=CC=CC=2)C1=O>C(#N)C>[Br:4][C:5]1[C:10]([CH3:11])=[CH:9][C:8]([N+:12]([O-:14])=[O:13])=[CH:7][C:6]=1[CH2:15][NH2:16]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 53328541HCID 53328541, compound

Product 1

HCID 53328542HCID 53328542, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4.4 mL of hydrazine hydrate was added to 2-[(2-bromo-3-methyl-5-nitrophenyl)methyl]-2,3-dihydro-1H-isoindole-1,3-dione (4.4 g, 11.7 mmol) in 220 mL of acetonitrile. The mixture was stirred under reflux overnight and then was allowed to cool to room temperature. The phtalhydrazide side product was remove by filtration and washed with 100 mL portions of acetonitrile. The combined acetonitrile filtrates were evaporated and the residue was partitioned between water and ethyl acetate. The organic layer was extracted with two 100 mL portions of aqueous HCl 1 M. The combined acidic aqueous layers were basified to pH=10 with solid potassium hydroxide and then extracted with ethyl acetate. The organic layer was dried over Na2SO4 filtered and evaporated to yield expected compound as an orange solid (2.15 g, 75% yield). m/z (ESI) 245.0 [M+H]+;

Workup

  1. temperatureunder reflux overnight
  2. customThe phtalhydrazide side product was remove by filtration
  3. washwashed with 100 mL portions of acetonitrile
  4. customThe combined acetonitrile filtrates were evaporated
  5. customthe residue was partitioned between water and ethyl acetate
  6. extractionThe organic layer was extracted with two 100 mL portions of aqueous HCl 1 M
  7. extractionextracted with ethyl acetate
  8. dry with materialThe organic layer was dried over Na2SO4
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-7a936cd1e6274d458a0c29a36298b048
Source dataset
uspto-grants-2014_03
Patent number
US08680095B2

Reaction notes

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