Nitroethane → 6-chloro-5-fluoro-3-(2-nitro-propenyl)-1H-indole

HRID 555337Notes

Reaction equation

HRID 555337 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]=O)=[CH:7][NH:8]2)=[CH:4][C:3]=1[F:13].C([O-])(=O)C.[NH4+].[N+:19]([CH2:22][CH3:23])([O-:21])=[O:20]>>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]=[C:22]([N+:19]([O-:21])=[O:20])[CH3:23])=[CH:7][NH:8]2)=[CH:4][C:3]=1[F:13]

Participants

4

Reactant 3

HCID 6587NitroethaneHCID 517165Ammonium AcetateHCID 210715286-chloro-5-fluoro-1H-indole-3-carbaldehyde

Product 1

HCID 669644686-chloro-5-fluoro-3-(2-nitro-propenyl)-1H-indoleYield 97%

Procedure

The solution (0.2 M) of 6-chloro-5-fluoro-1H-indole-3-carbaldehyde (4.0 g, 20.24 mmol) in nitroethane (100 mL) was refluxed with ammonium acetate (1.32 g, 0.85 mmol) for 4 hours. The reaction mixture was concentrated under vacuum to remove nitroethane, diluted with ethylacetate and washed with brine. The organic layer was concentrated to give 6-chloro-5-fluoro-3-(2-nitro-propenyl)-1H-indole (5.0 g, 97%) as a reddish orange solid. 1H NMR (500 MHz, CDCl3): δ 8.77 (s, 1H), 8.32 (s, 1H), 7.58 (d, 1H, J=2.5 Hz), 7.54 (d, 1H, J=9 Hz), 7.50 (d, 1H, J=5.9 Hz), 2.52 (s, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customto remove nitroethane
  3. additiondiluted with ethylacetate
  4. washwashed with brine
  5. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-755dcd2c185e498db22d0f0139e27882
Source dataset
uspto-grants-2011_11
Patent number
US08053442B2

Reaction notes

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