Acetyl chloride → N-(5-fluoro-2-oxo-2,3-dihydro-1H-indol-7-yl)-acetamide

HRID 905718Notes

Reaction equation

HRID 905718 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([F:12])[CH:5]=[C:6]2[C:10]=1[NH:9][C:8](=[O:11])[CH2:7]2.C(N(CC)CC)C.[C:20](Cl)(=[O:22])[CH3:21]>O1CCCC1>[F:12][C:4]1[CH:5]=[C:6]2[C:10](=[C:2]([NH:1][C:20](=[O:22])[CH3:21])[CH:3]=1)[NH:9][C:8](=[O:11])[CH2:7]2

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 592500547-Amino-5-fluoroindolin-2-one

Product 1

HCID 66608895N-(5-fluoro-2-oxo-2,3-dihydro-1H-indol-7-yl)-acetamideYield 96.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A stirred solution of 7-amino-5-fluoro-1,3-dihydro-indol-2-one (1.0 g, 6 mmol) obtained from Example 4 in 30 ml of tetrahydrofuran was added with triethylamine (1.3 ml, 9 mmol). The solution was cooled down to 0° C. in an ice-water bath and added with acetyl chloride (1.3 ml, 9 mmol) dropwise. The resulting mixture was heated to reflux for 1.5 hours and cooled until precipitate was formed. The solid was filtered, washed with water (50 ml×3) and dried in vacuo to give N-(5-fluoro-2-oxo-2,3-dihydro-1H-indol-7-yl)-acetamide (1.2 g, 96%) as a white solid.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 1.5 hours
  3. temperaturecooled until precipitate
  4. customwas formed
  5. filtrationThe solid was filtered
  6. washwashed with water (50 ml×3)
  7. customdried in vacuo

Sources & evidence

ORD record
ord-8798eb44c04d402e98714fbbb541681d
Source dataset
uspto-grants-2011_09
Patent number
US08012966B2

Reaction notes

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