Hydrochloric Acid → HCID 68527429, compound

HRID 884112Notes

Reaction equation

HRID 884112 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:7]=[CH:8][C:9]=1[O:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][N:12]=1)[CH3:2].N1C=CC=CC=1.[Cl:33][C:34]1[CH:35]=[C:36]([CH:40]=[CH:41][C:42]=1[Cl:43])[C:37](Cl)=[O:38].Cl>C(O)C.[C].[Pd]>[Cl:33][C:34]1[CH:35]=[C:36]([CH:40]=[CH:41][C:42]=1[Cl:43])[C:37]([NH:17][C:14]1[CH:15]=[CH:16][C:11]([O:10][C:9]2[CH:8]=[CH:7][C:6]([CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:5][C:4]=2[O:3][CH2:1][CH3:2])=[N:12][CH:13]=1)=[O:38]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 76403Benzoyl chloride, 3,4-dichloro-HCID 68526244HCID 68526244, compound

Product 1

HCID 68527429HCID 68527429, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of ethyl 3-[3-ethoxy-4-(5-nitropyridin-2-yloxy)phenyl]propionate (0.82 g, 2.3 mmol) in ethanol (40 mL) was added 10% palladium-carbon (0.15 g) under a nitrogen atmosphere, and the resulting solution was stirred under a hydrogen atmosphere at atmospheric pressure for 1 hour at room temperature. The palladium-carbon was removed by filtration, and the filtrate was concentrated. The obtained filtrate (0.58 g) was dissolved in dichloromethane (30 mL), and to the resulting solution were added pyridine (0.17 mL, 2.1 mmol) and 3,4-dichlorobenzoyl chloride (0.39 g, 1.84 mmol) under ice cooling. The resulting solution was stirred under ice cooling for 1 hour, and then stirred for 12 hours at room temperature. The reaction solution was made acidic by adding 10% hydrochloric acid, and extracted with dichloromethane. The dichloromethane layer was washed with a saturated sodium bicarbonate solution, dried over anhydrous magnesium sulfate, and evaporated, to thereby yield 0.94 g of the title compound.

Workup

  1. customThe palladium-carbon was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe obtained filtrate (0.58 g) was dissolved in dichloromethane (30 mL)
  4. stirringThe resulting solution was stirred under ice cooling for 1 hour
  5. stirringstirred for 12 hours at room temperature
  6. extractionextracted with dichloromethane
  7. washThe dichloromethane layer was washed with a saturated sodium bicarbonate solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customevaporated

Sources & evidence

ORD record
ord-cded67e6fe9446489c0b9d894539b884
Source dataset
uspto-grants-2012_08
Patent number
US08236826B2

Reaction notes

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