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

HRID 396455Notes

Reaction equation

HRID 396455 reaction equation
C[O:2][C:3](=[O:25])[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]([CH2:23][CH3:24])[CH:20]=[CH:19][N:18]=1)=[O:16].Cl>[OH-].[Na+].C(O)C>[Cl:14][C:10]1[CH:9]=[C:8]2[C:13]([C:5]([CH2:4][C:3]([OH:25])=[O:2])=[C:6]([C:15]([C:17]3[CH:22]=[C:21]([CH2:23][CH3:24])[CH:20]=[CH:19][N:18]=3)=[O:16])[NH:7]2)=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 23003267Methyl[6-chloro-2-(4-ethylpyridine-2-carbonyl)-1H-indol-3-yl]acetate

Product 1

HCID 18542263[6-Chloro-2-(4-ethylpyridine-2-carbonyl)-1H-indol-3-yl]acetic AcidYield 88.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A yellow suspension of methyl[6-chloro-2-(4-ethylpyridine-2-carbonyl)-1H-indol-3-yl]acetate (Example 57, 297 mg, 0.83 mmol) in 2N aqueous sodium hydroxide (2.5 ml) and ethanol (20 ml) was heated at reflux temperature for 3 h. After cooling to room temperature, the mixture was neutralized with 2N aqueous hydrochloric acid (2.5 ml) and concentrated. The residue was diluted with THF (150 ml), dried (MgSO4) and concentrated. The residual solids were recrystallization from ethyl acetate to give 251 mg (88%) of the title compound as yellow solids.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 3 h
  3. concentrationconcentrated
  4. additionThe residue was diluted with THF (150 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customrecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-1c348cea3a7f456d9e8cdddffcb0002e
Source dataset
uspto-grants-2003_08
Patent number
US06608070B1

Reaction notes

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