Hydrochloric Acid → 2-(2-(5-chloro-1H-indol-3-yl)ethylamino)-2-oxoacetic acid

HRID 58565

Reaction equation

HRID 58565 reaction equation
C(N(CC)CC)C.Cl.[Cl:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][CH:14]=[C:13]2[CH2:19][CH2:20][NH2:21].Cl[C:23](=[O:29])[C:24]([O:26]CC)=[O:25].[OH-].[Na+].Cl>ClCCl>[Cl:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][CH:14]=[C:13]2[CH2:19][CH2:20][NH:21][C:23](=[O:29])[C:24]([OH:26])=[O:25]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 20884Ethoxalyl chlorideHCID 28274945-Chloro-1H-indole-3-ethylamine monohydrochloride

Product 1

HCID 668319752-(2-(5-chloro-1H-indol-3-yl)ethylamino)-2-oxoacetic acidYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (2.28 mL; 16.22 mmol) was added to the mixture of 2-(5-chloro-1H-indol-3-yl)ethanamine hydrochloride (1.53 g; 6.49 mmol) and ethyl 2-chloro-2-oxoacetate (0.815 mL; 7.14 mmol) in dichloromethane (50 mL) at 0° C. After addition, the mixture was stirred at room temperature for 30 minutes and washed with an aqueous solution of sodium carbonate, dried over magnesium sulfate, and concentrated under reduced pressure. Ethanol (2 mL) and water (7.5 mL) were added to the resulting residue, followed by a 2M solution of sodium hydroxide (9.5 mL, 19 mmol). The mixture was stirred at room temperature for 20 minutes and the pH of the solution was adjusted to 1 by addition of a 6N hydrochloric acid. The precipitate was collected, and was dissolved in ethyl acetate. The ethyl acetate layer was dried over magnesium sulfate and was evaporated to dryness to give 1.36 g (81%) of 2-(2-(5-chloro-1H-indol-3-yl)ethylamino)-2-oxoacetic acid as a yellowish solid.

Workup

  1. additionAfter addition
  2. washwashed with an aqueous solution of sodium carbonate
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. additionEthanol (2 mL) and water (7.5 mL) were added to the resulting residue
  6. stirringThe mixture was stirred at room temperature for 20 minutes
  7. customThe precipitate was collected
  8. dissolutionwas dissolved in ethyl acetate
  9. dry with materialThe ethyl acetate layer was dried over magnesium sulfate
  10. customwas evaporated to dryness

Sources & evidence

ORD record
ord-a7d993b520b6444581f0b2e0f57d7396
Source dataset
uspto-grants-2016_09
Patent number
US09434722B2

Linked notes

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