Acetic Acid → methyl 6-chloro-2-methyl-1H-indole-3-carboxylate

HRID 2261842Notes

Reaction equation

HRID 2261842 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]([C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=1[N+:15]([O-])=O)=[C:5](O)[CH3:6].C(O)(=O)C>O.C(OCC)(=O)C.[Fe]>[CH3:1][O:2][C:3]([C:4]1[C:8]2[C:9](=[CH:10][C:11]([Cl:14])=[CH:12][CH:13]=2)[NH:15][C:5]=1[CH3:6])=[O:18]

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 587711412-(4-Chloro-2-nitro-phenyl)-3-hydroxy-but-2-enoic acid methyl ester

Product 1

HCID 57443356methyl 6-chloro-2-methyl-1H-indole-3-carboxylate

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of 2-(4-chloro-2-nitro-phenyl)-3-hydroxy-but-2-enoic acid methyl ester (4.66 g, 17.2 mmol), iron (5.76 g, 103 mmol) and glacial acetic acid (16 mL) is heated at 115° C. for 1 h and allowed to cool. The reaction mixture is diluted with water and ethyl acetate. The ethyl acetate layer is washed with brine and dried over MgSO4. The mixture of the title compound and a small amount of impurity is used in the next reaction without additional purification. ES/MS m/e 224.0 (M+1).

Workup

  1. temperatureto cool
  2. washThe ethyl acetate layer is washed with brine
  3. dry with materialdried over MgSO4
  4. additionThe mixture of the title compound
  5. customa small amount of impurity is used in the next reaction without additional purification

Sources & evidence

ORD record
ord-3e5d8346ee0f406cb3c0927a0c99d60f
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

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