Tetrabutylammonium Hydroxide → HCID 178433250, compound

HRID 1859071Notes

Reaction equation

HRID 1859071 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[CH:7]=O.[OH-].C([N+](CCCC)(CCCC)CCCC)CCC.[F:27][C:28]1[C:36]([N+:37]([O-:39])=[O:38])=[CH:35][CH:34]=[C:33]2[C:29]=1[CH2:30][C:31](=[O:40])[NH:32]2>>[F:27][C:28]1[C:36]([N+:37]([O-:39])=[O:38])=[CH:35][CH:34]=[C:33]2[C:29]=1/[C:30](=[CH:7]/[C:6]1[NH:5][CH:4]=[N:3][C:2]=1[CH3:1])/[C:31](=[O:40])[NH:32]2

Participants

4

Reactant 3

HCID 2723671Tetrabutylammonium HydroxideHCID 27958875-Methyl-1H-imidazole-4-carbaldehydeHCID 155126004-Fluoro-5-nitroindolin-2-one3×

Product 1

HCID 178433250HCID 178433250, compound

Procedure

To a solution of 1,3-dihydro4-fluoro-5-nitro-2H-indol-2-one (1 g, 5 mmol) in MeOH (10 mL) (Starting Material 10), was successively added, at r.t., 4-methyl-5-imidazolecarboxaldehyde (612 mg, 5.5 mmol) (Aldrich) and tetrabutyl ammonium hydroxide (11 mL, 1.0 M solution in MeOH)(Aldrich). The mixture was stirred at r.t. for 4 h. The resulting greenish precipitate was collected by suction filtration, washed with ether and air dried to yield (Z)-1,3-dihydro-4-fluoro-3-[(4-methyl-1H-imidazol-5-yl)methylene]-5-nitro-2H-indol-2-one as a green powder. (Yield 1.14 g, 79%).

Workup

  1. filtrationThe resulting greenish precipitate was collected by suction filtration
  2. washwashed with ether and air
  3. customdried

Sources & evidence

ORD record
ord-cad1eafb6b244bf18ad19a80fb435e96
Source dataset
uspto-grants-2000_11
Patent number
US06153634

Reaction notes

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