HCID 58899098, compound → HCID 57589732, compound

HRID 1674475Notes

Reaction equation

HRID 1674475 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[CH:13]=[CH:14][CH:15]=[C:16]3[C:21]=2[N:20]=[CH:19][CH:18]=[CH:17]3)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]>C(O)(=O)C.[Pt](=O)=O>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12]2[CH:13]=[CH:14][CH:15]=[C:16]3[C:21]=2[NH:20][CH2:19][CH2:18][CH2:17]3)=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 58899098HCID 58899098, compound

Product 1

HCID 57589732HCID 57589732, compoundYield 100.2%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 2.46 grams of N-(4-tert-butylphenyl)quinolin-8-amine from Step A in 100 mL of acetic acid containing 0.15 grams of platinum(IV) oxide was hydrogenated at 45 psi for 1.5 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 2.5 grams of dark blue oil. The oil was chromatographed on silica gel, eluting with hexane/ethyl acetate (20:1) to afford 2.0 grams of the desired product as a yellow oil. 1H NMR (CDCl3) δ 7.2 (d, 2H), 6.5-6.95 (m, 5H), 4.95 (bs, 1H), 3.3 (t, 2H), 2.8 (t, 2H), 1.9 (p, 2H), 1.3 (s, 9H).

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-1e4ef19e05574e1f831c465a5093827d
Source dataset
uspto-grants-2011_08
Patent number
US08003583B2

Reaction notes

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