Methyl iodide → 1-methyl-5-nitro-1H-indole-2-carboxylic acid

HRID 2053229Notes

Reaction equation

HRID 2053229 reaction equation
C([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([N+:15]([O-:17])=[O:16])=[CH:10][CH:9]=2)=[O:5])C.[H-].[Na+].I[CH3:21]>CN(C=O)C.CCCCCCC>[CH3:21][N:7]1[C:8]2[C:13](=[CH:12][C:11]([N+:15]([O-:17])=[O:16])=[CH:10][CH:9]=2)[CH:14]=[C:6]1[C:4]([OH:3])=[O:5]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 280312Ethyl 5-nitro-1H-indole-2-carboxylate

Product 1

HCID 124775361-methyl-5-nitro-1H-indole-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8900HeptaneSolvent

Procedure

5-Nitro-1H-indole-2-carboxylic acid ethyl ester (234 mg, 1 mmol) was dissolved in DMF (2 ml). NaH (32 mg, 1.4 mmol) was added as a suspension in heptane (0.5 ml) and the mixture was stirred at room temperature for 10 min. Iodomethane (170 mg, 1.2 mmol) was added drop-wise and the solution was left stirring for 1 h. During this reaction, hydrolysis occurred. The reaction mixture was quenched with H2O (2 ml) and washed with EtOAc (3×1 ml). The aqueous layer was acidified to pH 1 with conc. HCl until a white precipitate formed and extracted with EtOAc (3×1 ml). These organic layer were combined, dried (MgSO4), filtered and the solvent removed in vacuo to give the title compound.

Workup

  1. waitthe solution was left
  2. stirringstirring for 1 h
  3. customDuring this reaction, hydrolysis
  4. customThe reaction mixture was quenched with H2O (2 ml)
  5. washwashed with EtOAc (3×1 ml)
  6. customformed
  7. extractionextracted with EtOAc (3×1 ml)
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-fcbe54f057d747d39460fe74362366cd
Source dataset
uspto-grants-2008_02
Patent number
US07326732B2

Reaction notes

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