Pyrrole-2-carboxaldehyde → (Z)-1,3-Dihydro-4-fluoro-5-nitro-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one

HRID 1531151Notes

Reaction equation

HRID 1531151 reaction equation
[F:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][C:5](=[O:14])[NH:6]2.[NH:15]1[CH:19]=[CH:18][CH:17]=[C:16]1[CH:20]=O.[OH-].C([N+](CCCC)(CCCC)CCCC)CCC>CO>[F:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]2[C:3]=1/[C:4](=[CH:20]/[C:16]1[NH:15][CH:19]=[CH:18][CH:17]=1)/[C:5](=[O:14])[NH:6]2

Participants

5

Reactant 3

HCID 13854Pyrrole-2-carboxaldehydeHCID 2723671Tetrabutylammonium HydroxideHCID 155126004-Fluoro-5-nitroindolin-2-one2×

Product 1

HCID 21253427(Z)-1,3-Dihydro-4-fluoro-5-nitro-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1,3-dihydro-4-fluoro-5-nitro-2H-indol-2-one (400 mg, 2.04 mmol) (Starting Material 10) in MeOH (4 mL), was successively added at room temperature pyrrole-2-carboxaldehyde (220 mg, 2.25 mmol) (Aldrich) and tetrabutyl ammonium hydroxide (4.5 mL, 1.0 M solution in MeOH)(Aldrich). The mixture was stirred at r.t. for 12 h, then quenched with 1N HCl. The yellow precipitate was collected by suction filtration, washed with water and dried in a vacuum oven. (Yield 510 mg, 92%).

Workup

  1. customquenched with 1N HCl
  2. filtrationThe yellow precipitate was collected by suction filtration
  3. washwashed with water
  4. customdried in a vacuum oven

Sources & evidence

ORD record
ord-3c4d87cdfe27459487a37b92a311bb7d
Source dataset
uspto-grants-2001_03
Patent number
US06197804B1

Reaction notes

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