2-chloro-N-(3-methoxyphenyl)acetamide → 6-hydroxy-2,3-dihydro-1H-indol-2-one

HRID 241594Notes

Reaction equation

HRID 241594 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12]C)[CH:7]=1)=[O:4].[Al+3].[Cl-].[Cl-].[Cl-]>Cl>[OH:12][C:8]1[CH:7]=[C:6]2[C:11]([CH2:2][C:3](=[O:4])[NH:5]2)=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 286672-chloro-N-(3-methoxyphenyl)acetamideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 27841396-hydroxy-2,3-dihydro-1H-indol-2-oneYield 62.9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
120 °C

Procedure

2-chloro-N-(3-methoxyphenyl)acetamide (3.1 g, 16 mmol) and anhydrous AlCl3 powder (4.4 g, 32 mmol) is heated and stirred at 120° C. for 10 minutes and exhibit a melting state. The temperature is elevated gradually to 240° C. in 40 minutes and then stirred 5 minutes. The reaction is allowed to cool to obtain a brown powder. The solid powder is poured into a mixture of 100 g of crushed ice and 50 ml of concentrated hydrochloric acid. The mixture is stirred for 10 minutes and then reflux for 10 minutes, and allowed to cool to precipitate a light yellow powder, which is filtered out and recrystallized in water to obtain 1.5 g of 6-hydroxy-indoline-2-one, with a yield of 62%.

Workup

  1. waitThe temperature is elevated gradually to 240° C. in 40 minutes
  2. stirringstirred 5 minutes
  3. temperatureto cool
  4. customto obtain a brown powder
  5. stirringThe mixture is stirred for 10 minutes
  6. temperaturereflux for 10 minutes
  7. temperatureto cool
  8. customto precipitate a light yellow powder, which
  9. filtrationis filtered out
  10. customrecrystallized in water

Sources & evidence

ORD record
ord-b210808b85d5456cabf8a9ef62383e26
Source dataset
uspto-grants-2014_02
Patent number
US08653069B2

Reaction notes

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