4-Fluoroaniline → HCID 117014204, compound

HRID 1477596Notes

Reaction equation

HRID 1477596 reaction equation
[OH:1][CH:2]1[CH2:6][CH2:5][O:4][C:3]1=O.[F:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1.[OH-].[Na+]>ClCCl>[F:8][C:9]1[CH:15]=[CH:14][C:12]([N:13]2[CH2:5][CH2:6][CH:2]([OH:1])[C:3]2=[O:4])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 97314-FluoroanilineHCID 14798Sodium HydroxideHCID 545831alpha-Hydroxy-gamma-butyrolactone

Product 1

HCID 117014204HCID 117014204, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 3-hydroxydihydrofuran-2(3H)-one (5.00 g, 49.0 mmol) and 4-fluoroaniline (6.53 g, 59.0 mmol) was stirred at 150° C. for 1 day. After completion of the reaction, dichloromethane and 10 M sodium hydroxide aqueous solution were added to the reaction solution and the resultant mixture was filtered. To the filtrate, dichloromethane and concentrated hydrochloric acid were added to adjust pH to 1. The obtained solid was collected by filtration, washed with water, and dried under reduced pressure to obtain the title compound (6.78 g, yield 71%).

Workup

  1. additionwere added to the reaction solution
  2. filtrationthe resultant mixture was filtered
  3. additionTo the filtrate, dichloromethane and concentrated hydrochloric acid were added
  4. filtrationThe obtained solid was collected by filtration
  5. washwashed with water
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-01b97bbf7c4241aea282884ad9c06942
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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