Triethylamine → HCID 66637141, compound

HRID 1094667Notes

Reaction equation

HRID 1094667 reaction equation
[C:1]([C:5]1[CH:14]=[C:13]2[C:8]([C:9](Cl)=[C:10]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:11]=[N:12]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C>C(O)C.[C].[Pd]>[C:1]([C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[C:10]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:11]=[N:12]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 66637025HCID 66637025, compound

Product 1

HCID 66637141HCID 66637141, compoundYield 92.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A solution of ethyl 7-tert-butyl-4-chloroquinoline-3-carboxylate (2.06 g, 7.06 mmol) and triethylamine (1.97 ml, 21.2 mmol) in ethanol (70 ml) was hydrogenated over 5% palladium-carbon (300 mg) at balloon pressure for 1.5 hours. After the catalyst was filtered through a pad of celite, the filter cake was washed with CH2Cl2. The filtrate and washings were evaporated in vacuo to give crude product, which was purified by column chromatography on silica gel with hexane-ethyl acetate (8:1) to give the title compound (1.68 g, 92.5%) as yellow colored oil. 1H NMR (270 MHz, CDCl3) δ ppm 1.43-1.51 (3H, m), 1.45 (9H, s), 4.48 (2H, q, J=7.0 Hz), 6.69-7.75 (1H, m), 7.85-7.91 (1H, m), 8.13 (1H, s), 6.79-8.82 (1H, m), 9.41-9.44 (1H, m).

Workup

  1. filtrationAfter the catalyst was filtered through a pad of celite
  2. washthe filter cake was washed with CH2Cl2
  3. customThe filtrate and washings were evaporated in vacuo
  4. customto give crude product, which
  5. customwas purified by column chromatography on silica gel with hexane-ethyl acetate (8:1)

Sources & evidence

ORD record
ord-f9454d2713ba422e9d372a7b28f3531d
Source dataset
uspto-grants-2012_03
Patent number
US08134004B2

Reaction notes

Loading…