Acetonitrile → 6-Chloro-5-(4-methoxy-phenyl)-1H-indole-3-carbaldehyde

HRID 1054652Notes

Reaction equation

HRID 1054652 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1.[CH3:19]C#N.[OH-:22].[Na+]>O>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:19]=[O:22])=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 14798Sodium HydroxideHCID 866986576-Chloro-5-(4-methoxyphenyl)-1H-indole

Product 1

HCID 866986566-Chloro-5-(4-methoxy-phenyl)-1H-indole-3-carbaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

6-Chloro-5-(4-methoxy-phenyl)-1H-indole (25.0 g, 97 mmol), (chloromethylene)dimethyliminium chloride (18.8 g, 147 mmol) and MeCN (100 mL) were stirred at room temperature for 20 minutes. To the resulting bright yellow slurry was added 1 N NaOH (400 mL, 400 mmol) and water (400 mL). The reaction mixture was heated to 100° C. for 45 minutes, then cooled to 0° C. The slurry was filtered, and the collected solid was washed with water and air dried to afford the title compound as a yellow solid. MS (ES+) 286.5 (M+H)+. 1H NMR (400 MHz, CDCl3) δ 10.06 (s, 1 H), 8.74 (br. s., 1 H), 8.29 (s, 1 H), 7.87 (d, J=2.93 Hz, 1 H), 7.58 (s, 1 H), 7.42 (d, J=8.54 Hz, 2 H), 6.98 (d, J=8.54 Hz, 2 H), 3.88 (s, 3 H)

Workup

  1. temperaturecooled to 0° C
  2. filtrationThe slurry was filtered
  3. washthe collected solid was washed with water and air
  4. customdried

Sources & evidence

ORD record
ord-39b899c492044a609c8019530aff7db9
Source dataset
uspto-grants-2016_07
Patent number
US09394285B2

Reaction notes

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