Hydrazine hydrate (1:1) → HCID 23009596, compound

HRID 1678073Notes

Reaction equation

HRID 1678073 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][N:15]3C(=O)C4C(=CC=CC=4)C3=O)=[CH:9][CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.O.NN>C(O)C>[N:1]1([C:7]2[CH:8]=[CH:9][C:10]([CH2:13][CH2:14][NH2:15])=[CH:11][CH:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67309766HCID 67309766, compound

Product 1

HCID 23009596HCID 23009596, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Step 2 A solution of 2-[2-(4-morpholin-4-ylphenyl)ethyl]-1H-isoindole-1,3(2H)-dione (193 mg, 0.57 mmol) and hydrazine monohydrate (70 mg, 1.4 mmol) in ethanol (6 ml) was heated at reflux for 2 hr. The reaction was cooled to ambient temperature, and the solvent was removed in vacuo. The residue was taken up in ether, washed with 2M aqueous sodium hydroxide, and then extracted with 1M aqueous hydrochloric acid (2×10 mL). The acidic extracts were combined and the pH raised to 10-11 with 4M aqueous sodium hydroxide. This was then extracted thrice with ether, the organics combined, and dried (Na2SO4). Filtration and removal of solvent in vacuo left a brown oil, 110 mg, 0.57 mmol, 100 percent crude yield. The material was used without further purification.

Workup

  1. temperatureat reflux for 2 hr
  2. customthe solvent was removed in vacuo
  3. washwashed with 2M aqueous sodium hydroxide
  4. extractionextracted with 1M aqueous hydrochloric acid (2×10 mL)
  5. temperaturethe pH raised to 10-11 with 4M aqueous sodium hydroxide
  6. extractionThis was then extracted thrice with ether
  7. dry with materialdried (Na2SO4)
  8. filtrationFiltration and removal of solvent in vacuo
  9. waitleft a brown oil, 110 mg, 0.57 mmol, 100 percent crude yield
  10. customThe material was used without further purification

Sources & evidence

ORD record
ord-2b1fc394b2844c45ae1bfd9c212b7122
Source dataset
uspto-grants-2011_08
Patent number
US08008487B2

Reaction notes

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