HCID 67326287, compound → HCID 67324955, compound

HRID 871872Notes

Reaction equation

HRID 871872 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]2[CH2:13][CH2:14][N:15]([CH2:18][CH2:19][C:20]([F:23])([F:22])[F:21])[CH2:16][CH:17]=2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-])=O>C(O)C.C(O)(=O)C.[Pt](=O)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][C:20]([F:23])([F:21])[F:22])[CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[NH2:9]

Participants

4

Reactant 1

HCID 67326287HCID 67326287, compound

Product 1

HCID 67324955HCID 67324955, compoundYield 99.2%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 18476134Acetic acid ethanolSolvent

Procedure

1.65 g (5.0 mmol) of the product prepared in step 16.2 are placed in 120 mL of an ethanol/acetic acid mixture (v/v=1/1) in a hydrogenation autoclave, and 0.150 g of platinum (IV) oxide is added, under an inert atmosphere. The mixture is stirred under a hydrogen pressure of 4 bar at room temperature for 4 hours. After filtering through thin glass fibre paper and evaporating to dryness under reduced pressure, the oily residue is taken up in chloroform and washed with aqueous 1N NaOH solution. The organic phase is dried over Na2SO4, filtered and concentrated under vacuum. 1.5 g of the expected product are obtained in the form of a brown oil, which is used as obtained in the following step. Crude yield=quantitative.

Workup

  1. additionis added, under an inert atmosphere
  2. filtrationAfter filtering through thin glass fibre paper
  3. customevaporating to dryness under reduced pressure
  4. washwashed with aqueous 1N NaOH solution
  5. dry with materialThe organic phase is dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-28e1e456d4f8436ab9c89867c89549bf
Source dataset
uspto-grants-2015_03
Patent number
US08975250B2

Reaction notes

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