Hydrazine hydrate (1:1) → HCID 18348528, compound

HRID 2268476Notes

Reaction equation

HRID 2268476 reaction equation
[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[C:10]([O:14][CH3:15])[C:9]([O:16][CH3:17])=[C:8]2[C:4]=1[CH2:5][CH:6]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][N:26]1C(=O)C3=CC=CC=C3C1=O)[CH2:7]2.O.NN>C(O)C>[CH3:17][O:16][C:9]1[C:10]([O:14][CH3:15])=[C:11]([O:12][CH3:13])[C:3]([O:2][CH3:1])=[C:4]2[C:8]=1[CH2:7][CH:6]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][NH2:26])[CH2:5]2

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 18348600N-[8-(4,5,6,7-tetramethoxyindan-2-yl)octyl]phthalimide

Product 1

HCID 18348528HCID 18348528, compoundYield 91.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of N-[8-(4,5,6,7-tetramethoxyindan-2-yl)octyl]phthalimide (384 mg), hydrazine monohydrate (194 mg) in ethanol (8 ml) was heated under reflux for 6 hr. The reaction mixture was cooled to room temperature and solid was filtered off and the filtrate was concentrated. The residue was diluted with ethyl acetate, washed with 1M aqueous potassium carbonate, water, and saturated aqueous sodium chloride, and dried. The solvent was removed in vacuo to yield the entitled compound (260 mg) as an oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 6 hr
  3. filtrationsolid was filtered off
  4. concentrationthe filtrate was concentrated
  5. additionThe residue was diluted with ethyl acetate
  6. washwashed with 1M aqueous potassium carbonate, water, and saturated aqueous sodium chloride
  7. customdried
  8. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-904bc13e562e495a9b4be68fed61e858
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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