Hydrochloric Acid → 3-(4-Chlorophenoxy)-5-fluoro-2-methyl-1H-indole-1-acetic acid

HRID 2233737Notes

Reaction equation

HRID 2233737 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:27]=[CH:26][C:7]([O:8][C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([F:18])[CH:16]=3)[N:11]([CH2:19][C:20]([O:22]CC)=[O:21])[C:10]=2[CH3:25])=[CH:6][CH:5]=1.O.Cl>C1COCC1>[Cl:3][C:4]1[CH:27]=[CH:26][C:7]([O:8][C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([F:18])[CH:16]=3)[N:11]([CH2:19][C:20]([OH:22])=[O:21])[C:10]=2[CH3:25])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 116391123-(4-Chlorophenoxy)-5-fluoro-2-methyl-1H-indole-1-acetic acid, ethyl ester

Product 1

HCID 116885733-(4-Chlorophenoxy)-5-fluoro-2-methyl-1H-indole-1-acetic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2M sodium hydroxide (3 ml) was added to a stirred mixture of the product from step (ii) (0.36 g), water (10 ml) and THF (10 ml). After 2 h the solution was acidified with 2M hydrochloric acid and extracted with diethylether. The organics were washed with water, dried and evaporated under reduced pressure. The residue was recrystallised from diethylether/isohexane. Yield 138 mg

Workup

  1. extractionextracted with diethylether
  2. washThe organics were washed with water
  3. customdried
  4. customevaporated under reduced pressure
  5. customThe residue was recrystallised from diethylether/isohexane

Sources & evidence

ORD record
ord-c636743e688149c7b8e3cbf368770efb
Source dataset
uspto-grants-2010_05
Patent number
US07709521B2

Reaction notes

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