Formic Acid → N-(2-oxo-2,3-dihydro-1H-indol-5-yl)-formamide

HRID 2365028Notes

Reaction equation

HRID 2365028 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.C(O)=O.[NH2:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16](=[O:21])C2>O1CCCC1.N1CCCCC1>[O:7]=[C:5]1[CH2:6][C:20]2[C:12](=[CH:13][CH:14]=[C:18]([NH:17][CH:16]=[O:21])[CH:19]=2)[NH:11]1

Participants

6

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 27732135-Amino-2-oxindole

Product 1

HCID 23439025N-(2-oxo-2,3-dihydro-1H-indol-5-yl)-formamideYield 85%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8082PiperidineSolvent

Procedure

A solution of acetic anhydride (1.6 ml) and formic acid (1.2 ml) was stirred for 1 hour at room temperature, and added with 5-amino-1,3-dihydro-indol-2-one (3.56 g, 24 mmol, prepared according to U.S. Pat. No. 6,114,371) in 60 ml of tetrahydrofuran and piperidine (0.04 ml). The resulting mixture was stirred for 3 hours at room temperature until a precipitate was formed. The solid was filtered and recrystallized from methanol to give N-(2-oxo-2,3-dihydro-1H-indol-5-yl)-formamide (3.6 g, 85%) as a white solid.

Workup

  1. customprepared
  2. customwas formed
  3. filtrationThe solid was filtered
  4. customrecrystallized from methanol

Sources & evidence

ORD record
ord-29d147c4b6a54267bd7ea83cad5fc04b
Source dataset
uspto-grants-2014_04
Patent number
US08697692B2

Reaction notes

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