Acetyl chloride → Indole, 3-acetyl-5-nitro-

HRID 966056Notes

Reaction equation

HRID 966056 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2)([O-:3])=[O:2].[C:13](Cl)(=[O:15])[CH3:14].[Sn](Cl)(Cl)(Cl)Cl.C([O-])(O)=O.[Na+]>C(Cl)Cl.CN(C=O)C>[C:13]([C:7]1[C:6]2[C:10](=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[NH:9][CH:8]=1)(=[O:15])[CH3:14]

Participants

7

Reactant 4

HCID 6367Acetyl chlorideHCID 225235-NitroindoleHCID 24287Tin tetrachlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 20900Indole, 3-acetyl-5-nitro-Yield 99%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 5-nitroindole (10 g, 61.6 mmol) and acetyl chloride (5.8 g, 74 mmol) in methylene chloride at 0° C. is treated with tin tetrachloride (1M in CH2Cl2, 68 mL), stirred under N2 for 6 h, treated with saturated NaHCO3 to pH 9 and filtered. The filtrate is concentrated in vacuo to give a residue. The residue is dissolved in DMF and filtered. This filtrate is concentrated in vacuo to give the title product, 12.6 g (99% yield), identified by NMR and mass spectral analyses.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate is concentrated in vacuo
  3. customto give a residue
  4. filtrationfiltered
  5. concentrationThis filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-a82ae2ec0e2041e38687d86285c1a88c
Source dataset
uspto-grants-2005_10
Patent number
US06951881B2

Reaction notes

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