Ethyl Acetate → HCID 57589727, compound

HRID 1674477Notes

Reaction equation

HRID 1674477 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]=[C:14]2[C:19](=[CH:20][CH:21]=1)[N:18]=[CH:17][CH:16]=[CH:15]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]=[C:14]2[C:19](=[CH:20][CH:21]=1)[NH:18][CH2:17][CH2:16][CH2:15]2

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 58899097HCID 58899097, compound

Product 1

HCID 57589727HCID 57589727, compoundYield 77.4%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 7.00 grams of N-2-naphthylquinolin-6-amine from above in acetic acid (60 mL) and ethyl acetate (10 mL) containing 0.55 grams of platinum(IV) oxide was hydrogenated at 45 psi for 6.0 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 5.5 grams solid. The solid was chromatographed on silica gel, eluting with hexane/ethyl acetate gradient to afford 3.5 grams of the desired product as a yellow solid. 1H NMR (CDCl3/D2O) δ 6.4-7.8 (m, 10H), 3.1-3.5 (m, 2H), 2.6-2.9 (m, 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-66a881a052794a46b31abf4989c134df
Source dataset
uspto-grants-2011_08
Patent number
US08003583B2

Reaction notes

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