2-Chloroaniline → HCID 117770203, compound

HRID 1526332Notes

Reaction equation

HRID 1526332 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])O[C:4](=[O:9])[CH:3]=1.[Cl:10][C:11]1[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=1[NH2:13]>ClC1C=CC=CC=1Cl>[Cl:10][C:11]1[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=1[N:13]1[C:6]([CH3:8])=[CH:7][C:2]([OH:1])=[CH:3][C:4]1=[O:9]

Participants

4

Reactant 2

HCID 72402-ChloroanilineHCID 546757574-Hydroxy-6-methyl-2-pyrone

Product 1

HCID 117770203HCID 117770203, compoundYield 27.8%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
165 °C

Procedure

To a mixture of 4-hydroxy-6-methyl-2H-pyran-2-one (10.0 g) and 1,2-dichlorobenzene (9.91 mL) was added 2-chloroaniline (10.1 g) over 10 min at 165° C., and the reaction mixture was stirred at 165° C. for 30 min, and cooled to room temperature. The resulting solid was collected by filtration, and washed with dichloromethane to give the title compound (5.19 g).

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe resulting solid was collected by filtration
  3. washwashed with dichloromethane

Sources & evidence

ORD record
ord-936d77f94d284003a7073075555c2de4
Source dataset
uspto-grants-2015_07
Patent number
US09085578B2

Reaction notes

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