Hydrochloric Acid → [6-Chloro-2-(4-chloropyridine-2-carbonyl)-1H-indol-3-yl]acetic Acid

HRID 396438Notes

Reaction equation

HRID 396438 reaction equation
C[O:2][C:3](=[O:24])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][C:10]([Cl:14])=[CH:11][CH:12]=2)[NH:7][C:6]=1[C:15]([C:17]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][N:18]=1)=[O:16].Cl>C(O)C.[OH-].[Na+]>[Cl:14][C:10]1[CH:9]=[C:8]2[C:13]([C:5]([CH2:4][C:3]([OH:24])=[O:2])=[C:6]([C:15]([C:17]3[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][N:18]=3)=[O:16])[NH:7]2)=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 23003320Methyl[6-chloro-2-(4-chloropyridine-2-carbonyl)-1H-indol-3-yl]acetate

Product 1

HCID 18542278[6-Chloro-2-(4-chloropyridine-2-carbonyl)-1H-indol-3-yl]acetic AcidYield 94%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of methyl[6-chloro-2-[4-chloropyridine-2-carbonyl]-1H-indol-3-yl]acetate (Example 33, 195 mg, 0.537 mmol) in ethanol (20 ml) and 2N sodium hydroxide (4 ml) was heated for 1 h at 50° C. After cooling to room temperature, 2N hydrochloric acid (4 ml) was added and the mixture was concentrated. The residue was diluted in ethyl acetate (100 ml), washed with water (50 ml×2), and dried (MgSO4). After removal of solvent, the crystalline residue was recrystallized from ethyl acetate to afford 175 mg (94%) of the title compound.

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe mixture was concentrated
  3. additionThe residue was diluted in ethyl acetate (100 ml)
  4. washwashed with water (50 ml×2)
  5. dry with materialdried (MgSO4)
  6. customAfter removal of solvent
  7. customthe crystalline residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-58813a0a275a4f4287806d2d730a2c3e
Source dataset
uspto-grants-2003_08
Patent number
US06608070B1

Reaction notes

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