Ethyl Acetate → HCID 57589728, compound

HRID 1783288Notes

Reaction equation

HRID 1783288 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[NH:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:21]=1[N:20]=[CH:19][CH:18]=[CH:17]2.C(OCC)(=O)C>C(O)(=O)C.[Pt](=O)=O>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[NH:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:21]=1[NH:20][CH2:19][CH2:18][CH2:17]2

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 12418117HCID 12418117, compound

Product 1

HCID 57589728HCID 57589728, compoundYield 101.4%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 4.08 grams of N-2-naphthylquinolin-8-amine from above in acetic acid (10 mL) and ethyl acetate (150 mL) containing 0.24 grams of platinum(IV) oxide was hydrogenated at 45 psi for four hours on a Parr low-pressure hydrogenator. The solution was filtered through diatomaceous earth; concentrated in vacuo; and neutralized with 3N aqueous sodium hydroxide. The aqueous phase was diluted with water and extracted three times with ethyl acetate. The combined ethyl acetate layers were washed with brine; dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to yield 4.2 grams of the desired product as a purple oil. 1H NMR (CDCl3/D2O) δ 7.7 (m, 2H), 7.6 (d,1H), 7.35 (t, 1H), 7.25 (m, 1H), 7.05 (m, 2H), 6.9 (m, 2H), 6.6 (t, 1H), 3.3 (t, 2H), 2.85 (t, 2H), 1.95 (p, 2H).

Workup

  1. filtrationThe solution was filtered through diatomaceous earth
  2. concentrationconcentrated in vacuo
  3. additionThe aqueous phase was diluted with water
  4. extractionextracted three times with ethyl acetate
  5. washThe combined ethyl acetate layers were washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-993bc91a09f64394813bc9f46ed5fd8c
Source dataset
uspto-grants-2009_03
Patent number
US07501386B2

Reaction notes

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