Hydrochloric Acid → HCID 66758777, compound

HRID 1850413Notes

Reaction equation

HRID 1850413 reaction equation
O.NN.[Br:4][C:5]1[C:6]([CH3:29])=[C:7]([CH3:28])[C:8]2[O:12][C:11]([CH2:14][N:15]3C(=O)C4C(=CC=CC=4)C3=O)([CH3:13])[CH2:10][C:9]=2[C:26]=1[CH3:27].Cl.[OH-].[Na+]>C(O)C>[Br:4][C:5]1[C:6]([CH3:29])=[C:7]([CH3:28])[C:8]2[O:12][C:11]([CH2:14][NH2:15])([CH3:13])[CH2:10][C:9]=2[C:26]=1[CH3:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 66759768HCID 66759768, compound

Product 1

HCID 66758777HCID 66758777, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrazine monohydrate (87 mg, 1.73 mmol) was added to a solution of ethanol (13 mL) containing 2-[(5-bromo-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-2-yl)methyl]-1H-isoindole-1,3(2H)-dione (530 mg, 1.28 mmol) synthesized in Reference Example 129, and the mixture was stirred under heated reflux for 3 hours. The reaction solution was cooled to room temperature, and 6N hydrochloric acid (10 mL) was added thereto, followed by stirring under heated reflux for 1 hour. The reaction solution was cooled to room temperature, and then 1N sodium hydroxide aqueous solution was added thereto to become weakly basic, followed by extraction using diisopropyl ether. The organic layer was washed with saturated saline, and dried using anhydrous magnesium sulfate, followed by concentration under reduced pressure. The residue was purified by basic silica gel chromatography (hexane-ethyl acetate 80:20-0:100) to give 250 mg of the title compound (yield: 69%).

Workup

  1. customsynthesized in Reference Example 129
  2. temperatureunder heated
  3. temperaturereflux for 3 hours
  4. stirringby stirring
  5. temperatureunder heated
  6. temperaturereflux for 1 hour
  7. temperatureThe reaction solution was cooled to room temperature
  8. extractionfollowed by extraction
  9. washThe organic layer was washed with saturated saline
  10. customdried
  11. concentrationfollowed by concentration under reduced pressure
  12. customThe residue was purified by basic silica gel chromatography (hexane-ethyl acetate 80:20-0:100)

Sources & evidence

ORD record
ord-25f7f9d28f9d446e8fa3aa9fd356d6dc
Source dataset
uspto-grants-2015_02
Patent number
US08957069B2

Reaction notes

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