Triethylamine → 6-(2-Tert-butoxy-2-oxoethoxy)quinoline-3-carboxylic acid

HRID 2403690Notes

Reaction equation

HRID 2403690 reaction equation
C(N(CC)CC)C.[C:8]([O:12][C:13](=[O:30])[CH2:14][O:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[N:22]=[C:21](Cl)[C:20]([C:27]([OH:29])=[O:28])=[CH:19]2)([CH3:11])([CH3:10])[CH3:9].[H][H]>[Pd].CO>[C:8]([O:12][C:13](=[O:30])[CH2:14][O:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[N:22]=[CH:21][C:20]([C:27]([OH:29])=[O:28])=[CH:19]2)([CH3:11])([CH3:9])[CH3:10]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 866728696-(2-Tert-butoxy-2-oxoethoxy)-2-chloroquinoline-3-carboxylic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 708961456-(2-Tert-butoxy-2-oxoethoxy)quinoline-3-carboxylic acidYield 84.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

Methanol (100 mL) and triethylamine (4.5 mL, 33 mmol) were added to 6-(2-tert-butoxy-2-oxoethoxy)-2-chloroquinoline-3-carboxylic acid (1.27 g, 3.76 mmol). 10% Palladium on carbon (350 mg) was added and the reaction was pressurized to 17 psi hydrogen. The reaction was agitated at room temperature for 3 hours. The reaction mixture was diluted with methanol and filtered through Celite. The filtrate was concentrated to a yellow solid. The solid was diluted with water and the mixture was acidified to pH=4 with 1 N aqueous hydrochloric acid. The solid was collected by filtration, washed with water, and dried under vacuum to give the title compound (960 mg, 84%) as a pale yellow solid. +ESI (M+H) 304.2; 1H NMR (400 MHz, CD3OD, δ): 9.19 (d, J=2.15 Hz, 1 H), 8.87 (d, J=2.15 Hz, 1 H), 8.01 (d, J=9.36 Hz, 1 H), 7.59 (dd, J=9.27, 2.83 Hz, 1 H), 7.38 (d, J=2.73 Hz, 1 H), 4.78 (s, 2 H), 1.49 (s, 9 H).

Workup

  1. filtrationfiltered through Celite
  2. concentrationThe filtrate was concentrated to a yellow solid
  3. additionThe solid was diluted with water
  4. filtrationThe solid was collected by filtration
  5. washwashed with water
  6. customdried under vacuum

Sources & evidence

ORD record
ord-da5255198ac64c32bc1af8e909d89e6b
Source dataset
uspto-grants-2014_08
Patent number
US08802688B2

Reaction notes

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