Hydrazine hydrate (1:1) → HCID 18766464, compound

HRID 480695Notes

Reaction equation

HRID 480695 reaction equation
C1(=O)[N:5]([CH2:6][CH2:7][CH2:8][C:9]2[CH:10]=[C:11]([CH:23]=[CH:24][CH:25]=2)[O:12][C:13]([CH3:22])([CH3:21])[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])C(=O)C2=CC=CC=C12.O.NN>C(O)C>[NH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:10]=[C:11]([CH:23]=[CH:24][CH:25]=1)[O:12][C:13]([CH3:22])([CH3:21])[C:14]([O:16][C:17]([CH3:19])([CH3:20])[CH3:18])=[O:15]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 18766595HCID 18766595, compound

Product 1

HCID 18766464HCID 18766464, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

tert-Butyl 2-[3-(3-phthalimidopropyl)phenoxy]-2-methylpropionate (1.87 g, 4.41 mmol) was dissolved in ethanol (10.0 mL) Subsequently, hydrazine monohydrate (184 mg, 5.74 mmol) was added dropwise, and the mixture was stirred overnight at 80° C. Thereafter, the temperature of the mixture was returned to room temperature, and the mixture was subjected to filtration. The resultant filtrate was subjected to drying over sodium sulfate, concentration under reduced pressure, and purification by silica gel chromatography (chloroform/methanol (saturated with ammonia)=20/1), whereby the target compound was obtained (560 mg, 43%).

Workup

  1. customwas returned to room temperature
  2. filtrationthe mixture was subjected to filtration
  3. dry with materialto drying over sodium sulfate, concentration under reduced pressure, and purification by silica gel chromatography (chloroform/methanol (saturated with ammonia)=20/1), whereby the target compound
  4. customwas obtained (560 mg, 43%)

Sources & evidence

ORD record
ord-6d950d78e0d2418dae1fd18d5c592a3f
Source dataset
uspto-grants-2003_11
Patent number
US06653334B1

Reaction notes

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