Ethanol → HCID 57608193, compound

HRID 1171230Notes

Reaction equation

HRID 1171230 reaction equation
C(O)C.[CH2:4]([O:11][C:12]1[CH:13]=[CH:14][C:15]2[CH:19]=[C:18]([CH2:20][N:21]3C(=O)C4C(=CC=CC=4)C3=O)[S:17][C:16]=2[CH:32]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.O.NN>O>[CH2:4]([O:11][C:12]1[CH:13]=[CH:14][C:15]2[CH:19]=[C:18]([CH2:20][NH2:21])[S:17][C:16]=2[CH:32]=1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 57608231HCID 57608231, compound

Product 1

HCID 57608193HCID 57608193, compoundYield 107.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an ethanol (5 mL) solution of 2-(6-benzyloxy-benzo[b]thiophen-2-ylmethyl)-isoindole-1,3-dione (144 mg, 0.36 mmol) described in Production Example 77-1-4 was added hydrazine monohydrate (18.7 mg, 0.374 mmol). The mixture was stirred for 4 hours while heating under reflux. The reaction mixture was allowed to cool on standing followed by the addition of water and concentrating under a reduced pressure until the total volume of the solution was reduced by half. The solution was distributed between ethyl acetate and water. The organic layer was separated followed by washing with 2 N aqueous sodium hydroxide solution and water, drying over anhydrous magnesium sulfate and filtering. The filtrate was concentrated under a reduced pressure to obtain the title compound (104 mg, quantitative). This amine was used in the subsequent reaction without purifying.

Workup

  1. temperaturewhile heating
  2. temperatureunder reflux
  3. temperatureto cool
  4. concentrationconcentrating under a reduced pressure until the total volume of the solution
  5. customThe organic layer was separated
  6. washby washing with 2 N aqueous sodium hydroxide solution and water
  7. dry with materialdrying over anhydrous magnesium sulfate
  8. filtrationfiltering
  9. concentrationThe filtrate was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-23919fb59040457094ec7cb99cae054a
Source dataset
uspto-grants-2010_11
Patent number
US07829585B2

Reaction notes

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