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

HRID 338309Notes

Reaction equation

HRID 338309 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 1N 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, 1H), 8.74 (br. s., 1H), 8.29 (s, 1H), 7.87 (d, J=2.93 Hz, 1H), 7.58 (s, 1H), 7.42 (d, J=8.54 Hz, 2H), 6.98 (d, J=8.54 Hz, 2H), 3.88 (s, 3H)

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-1bd288b1d0804fa19f1453304d6f86e3
Source dataset
uspto-grants-2014_11
Patent number
US08889730B2

Reaction notes

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