Hydrochloric Acid → HCID 57868186, compound

HRID 1091319Notes

Reaction equation

HRID 1091319 reaction equation
C([O:3][C:4](=[O:26])[CH2:5][C:6]1[CH:11]=[C:10]([Cl:12])[C:9]([NH:13][C:14]([C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[NH:18][CH:17]=2)=[O:15])=[CH:8][C:7]=1[Cl:25])C.C1COCC1.[OH-].[Na+].Cl>C(O)C>[Cl:25][C:7]1[CH:8]=[C:9]([NH:13][C:14]([C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[NH:18][CH:17]=2)=[O:15])[C:10]([Cl:12])=[CH:11][C:6]=1[CH2:5][C:4]([OH:26])=[O:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 66591993HCID 66591993, compound

Product 1

HCID 57868186HCID 57868186, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

This [2,5-dichloro-4-[(1H-indol-3-ylcarbonyl)amino]phenyl]acetic acid ethyl ester (5.7 g, 14.57 mmol) was added to THF (50 mL) and ethanol (30 mL), and a 0.25N-aqueous solution of sodium hydroxide (120 mL) was added thereto. The mixture was stirred for 15 hours at room temperature, and then for one hour at 60° C. The reaction mixture was left to cool naturally to room temperature, and then 1N—HCl (32 mL) was added thereto while stirring the reaction mixture under ice cooling. Precipitated crystals were collected by filtration under reduced pressure, washed with water, and then dried, to obtain the title compound (4.25 g, 80%) as a solid.

Workup

  1. waitfor one hour at 60° C
  2. waitThe reaction mixture was left
  3. temperatureto cool naturally to room temperature
  4. stirringwhile stirring the reaction mixture under ice cooling
  5. customPrecipitated crystals
  6. filtrationwere collected by filtration under reduced pressure
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-94de425434fa4e468b3e62f3fc9b59ca
Source dataset
uspto-grants-2012_03
Patent number
US08129366B2

Reaction notes

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