Trifluoroacetic acid → 4-Chloro-2-methyl-1H-indole

HRID 489721Notes

Reaction equation

HRID 489721 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[C:9]=1[CH2:15][C:16](=O)[CH3:17])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Cl:14][C:10]1[C:9]([CH3:15])=[C:8]([NH2:7])[CH:13]=[CH:12][CH:11]=1.[Cl:14][C:10]1[CH:11]=[CH:12][CH:13]=[C:8]2[C:9]=1[CH:15]=[C:16]([CH3:17])[NH:7]2

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23589043HCID 23589043, compound

Product 2

HCID 68943-Chloro-2-methylanilineHCID 218145654-Chloro-2-methyl-1H-indoleYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the crude [3-Chloro-2-(2-oxo-propyl)-phenyl]-carbamic acid tert-butyl ester (5.21 g) in dichloromethane (180 ml) was added trifluoroacetic acid (20 ml). The reaction mixture was stirred at room temperature for 5 days and then partitioned between dichloromethane and 5% sodium bicarbonate solution. The organic extract was washed with brine, dried (anhydrous sodium sulfate), and concentrated under reduced pressure to give 4-Chloro-2-methyl-1H-indole and 3-Chloro-2-methyl-phenylamine as a mixture (2.6 g mixture, 69% yield of 4-Chloro-2-methyl-1H-indole). 1H NMR (CDCl3) d: 2.45 (s, 3H), 6.32-6.33 (m, 1H), 6.98-7.18 (m, 3H), 7.96 (bs, 1H), M−H: 164.

Workup

  1. custompartitioned between dichloromethane and 5% sodium bicarbonate solution
  2. extractionThe organic extract
  3. washwas washed with brine
  4. dry with materialdried (anhydrous sodium sulfate)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ddf44bf084ac4ec0852d230500edc18d
Source dataset
uspto-grants-2005_12
Patent number
US06979696B2

Reaction notes

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