Trifluoroacetic acid → 5-(4-Nitro-benzyl)-1,3-dihydro-indol-2-one

HRID 640840

Reaction equation

HRID 640840 reaction equation
FC(F)(F)C(O)=O.[BH4-].[Na+].[N+:10]([C:13]1[CH:30]=[CH:29][C:16]([C:17]([C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][CH:27]=2)[NH:24][C:23](=[O:28])[CH2:22]3)=O)=[CH:15][CH:14]=1)([O-:12])=[O:11]>>[N+:10]([C:13]1[CH:14]=[CH:15][C:16]([CH2:17][C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][CH:27]=2)[NH:24][C:23](=[O:28])[CH2:22]3)=[CH:29][CH:30]=1)([O-:12])=[O:11]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 4311764Sodium borohydrideHCID 687007145-(4-Nitro-benzoyl)-1,3-dihydro-indol-2-one

Product 1

HCID 687018775-(4-Nitro-benzyl)-1,3-dihydro-indol-2-oneYield 61%

Procedure

In a dried 250 mL round bottom flask, 20.73 mL of trifluoroacetic acid was added and then cooled to 0° C. under Ar(g). NaBH4 in pellet form (1.35 g, 35.71 mmol, ˜1.5 pellets) was added to the flask. 5-(4-Nitro-benzoyl)-1,3-dihydro-indol-2-one (as prepared in Example 7, 1.0 g, 3.55 mmol) was then added in slowly over 15 min. After the addition was completed, the reaction was allowed to warm to room temperature and was stirred for 36 hours forming a yellow foamy mixture. The mixture was poured over ice-water and allowed to warm to room temperature, during which a tan solid precipitated out of solution. The tan solid was collected by filtration and washed with water affording 5-(4-Nitro-benzyl)-1,3-dihydro-indol-2-one in 61% yield (0.589 g, 2.165 mmol).

Workup

  1. additionAfter the addition
  2. customforming a yellow foamy mixture
  3. temperatureto warm to room temperature, during which a tan solid
  4. customprecipitated out of solution
  5. filtrationThe tan solid was collected by filtration
  6. washwashed with water

Sources & evidence

ORD record
ord-025d31beb3b34cc494042ef893b0fd9b
Source dataset
uspto-grants-2010_04
Patent number
US07692005B2

Linked notes

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