Ammonium Chloride → HCID 19827438, compound

HRID 1494288Notes

Reaction equation

HRID 1494288 reaction equation
[Cl-:1].[NH4+].[OH:3][CH:4]([CH3:20])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][C:8]=1[NH:16][C:17](=[O:19])[CH3:18]>[Zn]>[ClH:1].[OH:3][CH:4]([CH3:20])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:8]=1[NH:16][C:17](=[O:19])[CH3:18]

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 198274242-Acetylamino-4-nitrophenyl beta-hydroxypropyl ether

Product 1

HCID 19827438HCID 19827438, compound

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Conditions

Temperature
-20 °C

Procedure

1.5 g of ammonium chloride and 37.5 g of powdered zinc are added to 70 ml of an aqueous-ethanolic solution (60 ml of C2H5OH/10 ml of H2O) and this mixture is preheated to the reflux temperature, with stirring. 0.048 mol (12.2 g) of 2-acetylamino-4-nitrophenyl β-hydroxypropyl ether is then added, the addition being adjusted so as to maintain the reflux without heating. When the addition has ended, the mixture is kept under reflux for 10 minutes and filtered at the boil onto a mixture of 5 ml of ethanol and 5.1 ml of 36% strength hydrochloric acid, cooled to -20° C. The expected product precipitates in the form of the monohydrochloride. It is filtered off, washed with a small amount of ice-cold ethanol and dried in vacuo at 50° C. It melts with decomposition at between 220° and 225° C.

Workup

  1. additionthe addition
  2. temperatureto maintain the
  3. temperaturereflux
  4. temperaturewithout heating
  5. additionWhen the addition
  6. temperatureunder reflux for 10 minutes
  7. filtrationfiltered at the boil onto a mixture of 5 ml of ethanol and 5.1 ml of 36% strength hydrochloric acid
  8. customThe expected product precipitates in the form of the monohydrochloride
  9. filtrationIt is filtered off
  10. washwashed with a small amount of ice-cold ethanol
  11. customdried in vacuo at 50° C
  12. custommelts with decomposition at between 220° and 225° C.

Sources & evidence

ORD record
ord-123eafb5291649339906a64993fb8d32
Source dataset
uspto-grants-1991_06
Patent number
US05026401

Reaction notes

Loading…