2-Amino-4-chlorophenol → 2-Acetylamino-4-chlorophenol

HRID 29857

Reaction equation

HRID 29857 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[OH:9].[C:10]([O:14]C)(C)(C)[CH3:11]>>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]([OH:9])=[C:2]([NH:1][C:10](=[O:14])[CH3:11])[CH:7]=1

Participants

3

Reactant 2

HCID 72652-Amino-4-chlorophenolHCID 15413tert-Butyl methyl ether

Product 1

HCID 952582-Acetylamino-4-chlorophenolYield 92%

Conditions

Temperature
22.5 °C

Procedure

143.6 g (1 mole) of 2-amino-4-chlorphenol was suspended in 550 ml of methyl t-butyl ether under mild nitrogen purge. The mixture was heated to reflux until the material was dissolved. After 40 minutes, 112.3 g of acetic anhydride was added. After the addition the mixture was cooled to 20-25° C. in one hour. After stirring for an additional hour the mixture was cooled to 0-5° C. under stirring and kept on this temperature for an additional hour. The product was filtered off, washed with 200 ml of methyl t-butyl ether twice and dried at 50° C. and 100 mbar under a gentle nitrogen stream till dry. Yield about 92%.

Workup

  1. custompurge
  2. temperatureThe mixture was heated
  3. temperatureto reflux until the material
  4. dissolutionwas dissolved
  5. addition112.3 g of acetic anhydride was added
  6. additionAfter the addition the mixture
  7. temperaturewas cooled to 0-5° C.
  8. stirringunder stirring
  9. waitkept on this temperature for an additional hour
  10. filtrationThe product was filtered off
  11. washwashed with 200 ml of methyl t-butyl ether twice
  12. customdried at 50° C.
  13. customtill dry

Sources & evidence

ORD record
ord-e1db0f8216b2401a958126e0e678b5bd
Source dataset
uspto-grants-2008_09
Patent number
US07423040B2

Linked notes

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