m-Chlorophenylhydrazine hydrochloride → [3-(6-Chloro-2-methyl-1H-indol-3-ylsulfanyl)-phenyl]-acetic acid

HRID 1466806Notes

Reaction equation

HRID 1466806 reaction equation
O=[C:2]([CH3:15])[CH2:3][S:4][C:5]1[CH:6]=[C:7]([CH2:11][C:12]([OH:14])=[O:13])[CH:8]=[CH:9][CH:10]=1.Cl.[Cl:17][C:18]1[CH:19]=[C:20]([NH:24]N)[CH:21]=[CH:22][CH:23]=1>CC(O)(C)C>[Cl:17][C:18]1[CH:19]=[C:20]2[C:21]([C:3]([S:4][C:5]3[CH:6]=[C:7]([CH2:11][C:12]([OH:14])=[O:13])[CH:8]=[CH:9][CH:10]=3)=[C:2]([CH3:15])[NH:24]2)=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 75331m-Chlorophenylhydrazine hydrochlorideHCID 66765032[3-(2-Oxo-propylsulfanyl)-phenyl]-acetic acid

Product 1

HCID 66765068[3-(6-Chloro-2-methyl-1H-indol-3-ylsulfanyl)-phenyl]-acetic acid

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
70 °C

Procedure

[3-(2-Oxo-propylsulfanyl)-phenyl]-acetic acid (3.69 g, 16.5 mmol) was dissolved in t-BuOH (100 mL) then 3-chlorophenylhydrazine hydrochloride (3.25 g, 18.15 mmol) was added. The reaction was heated to 70° C. for 2 hour then cooled and submitted to aqueous workup to afford a mixture of regioisomers which included the title compound. The crude material was brought forward to the next step without further purification.

Workup

  1. temperaturethen cooled
  2. customto afford
  3. additiona mixture of regioisomers which

Sources & evidence

ORD record
ord-d138c14bc629424b9f0a22a1388a2034
Source dataset
uspto-grants-2015_04
Patent number
US09000025B2

Reaction notes

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