Tin atom → HCID 14068942, compound

HRID 1904800Notes

Reaction equation

HRID 1904800 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]23[CH2:15][CH:14]2[C:13](=[O:16])[N:12]([CH2:17][C:18]#[CH:19])[C:11]3=[O:20])=[CH:6][CH:5]=1)([O-])=O.[Sn]>O>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]23[CH2:15][CH:14]2[C:13](=[O:16])[N:12]([CH2:17][C:18]#[CH:19])[C:11]3=[O:20])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 5352426Tin atomHCID 14068932HCID 14068932, compound

Product 1

HCID 14068942HCID 14068942, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
100 °C

Procedure

A mixture of 0.54 g of 1-(4-nitrophenyl)-3-propargyl-3-azabicyclo[3.1.0]hexane-2,4-dione and 1.5 g of tin powder in 4 ml of water and 4 ml of water is stirred for 1 hour at 100° C. The reaction mixture is cooled to room temperature and then diluted with 20 ml of water, filtered, and made alkaline with sodium hydroxide solution. The reaction mixture is extracted with ethyl acetate and the organic phase is washed with a dilute aqueous solution of sodium chloride until neutral, dried over magnesium sulfate and concentrated. The residue is recrystallised from ethyl acetate/petroleum ether, affording the title compound with m.p. 106°-109° C. and with Rf=0.12 on thin-layer silica gel plates in the system hexane/ethyl acetate (1:1).

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. filtrationfiltered
  3. extractionThe reaction mixture is extracted with ethyl acetate
  4. washthe organic phase is washed with a dilute aqueous solution of sodium chloride until neutral,
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue is recrystallised from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-032634403a034b0baafab54bc8b6277a
Source dataset
uspto-grants-1989_06
Patent number
US04839379

Reaction notes

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