Ethyl Acetate → HCID 57589728, compound

HRID 1674479Notes

Reaction equation

HRID 1674479 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-c323dbb2840643f4a5978aac758106f9
Source dataset
uspto-grants-2011_08
Patent number
US08003583B2

Reaction notes

Loading…