Ethanol → [5-Chloro-2-(4-methylpyridine-2-carbonyl)-1H-indol-3-yl]acetic Acid

HRID 396440Notes

Reaction equation

HRID 396440 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:14]([O-])=O)=[C:6]([CH:13]=1)/[CH:7]=[CH:8]/[C:9]([O:11]C)=[O:10].[Cl-].[NH4+:18].[CH2:19]([OH:21])[CH3:20]>[Fe].O>[Cl:1][C:2]1[CH:13]=[C:6]2[C:5](=[CH:4][CH:3]=1)[NH:14][C:20]([C:19]([C:8]1[CH:7]=[C:6]([CH3:13])[CH:5]=[CH:4][N:18]=1)=[O:21])=[C:7]2[CH2:8][C:9]([OH:11])=[O:10]

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 23003335Methyl trans-5-chloro-2-nitrocinnamate

Product 1

HCID 23003314[5-Chloro-2-(4-methylpyridine-2-carbonyl)-1H-indol-3-yl]acetic AcidYield 98%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

A mixture of methyl trans-5-chloro-2-nitrocinnamate (step 1, 3.00 g, 12.42 mmol), iron powder (3.65 g, 62.08 mmol), ammonium chloride (332 mg, 6.21 mmol), ethanol (60 ml) and water (10 ml) was heated at reflux temperature for 2 h. The mixture was cooled and filtered through a pad of Celite. The filtrate was concentrated. The residue was diluted with ethyl acetate (200 ml) and washed with water (100 ml×2). After drying (MgSO4), removal of solvent gave 2.57 g (98%) of the title compound as crystals.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 2 h
  3. temperatureThe mixture was cooled
  4. filtrationfiltered through a pad of Celite
  5. concentrationThe filtrate was concentrated
  6. additionThe residue was diluted with ethyl acetate (200 ml)
  7. washwashed with water (100 ml×2)
  8. customAfter drying
  9. custom(MgSO4), removal of solvent

Sources & evidence

ORD record
ord-1469b72e87454828986792c16c35004c
Source dataset
uspto-grants-2003_08
Patent number
US06608070B1

Reaction notes

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