Ammonium Chloride → 4-amino-N-tetrahydrofurfurylaniline dihydrochloride

HRID 26338Notes

Reaction equation

HRID 26338 reaction equation
[Cl-:1].[NH4+].[N+:3]([C:6]1[CH:18]=[CH:17][C:9]([NH:10][CH2:11][CH:12]2[O:16][CH2:15][CH2:14][CH2:13]2)=[CH:8][CH:7]=1)([O-])=O>[Zn]>[ClH:1].[ClH:1].[NH2:3][C:6]1[CH:7]=[CH:8][C:9]([NH:10][CH2:11][CH:12]2[O:16][CH2:15][CH2:14][CH2:13]2)=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 226105934-nitro-N-(tetrahydrofuran-2-ylmethyl)aniline

Product 1

HCID 204310384-amino-N-tetrahydrofurfurylaniline dihydrochloride

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

4.02 g of ammonium chloride and 57 g of zinc powder are added to 180 ml of an aqueous-alcoholic solution (83% of alcohol and 17% of water). This mixture is heated to the reflux temperature, whilst stirring, and 0.122 mol (27 g) of 4-nitro-N-tetrahydrofurfurylaniline is then added gradually. When the reaction medium is decolorised, it is filtered and the filtrate is collected in a flask containing 30 ml of ice-cooled hydrochloric acid (d=1.19). On cooling, the expected dihydrochloride precipitates in the form of crystals. It is filtered off and washed with absolute alcohol and then acetone. After drying in vacuo, it melts at about 190° C. with decomposition.

Workup

  1. temperatureThis mixture is heated to the reflux temperature
  2. filtrationit is filtered
  3. customthe filtrate is collected in a flask
  4. additioncontaining 30 ml of ice-
  5. temperaturecooled hydrochloric acid (d=1.19)
  6. temperatureOn cooling
  7. customthe expected dihydrochloride precipitates in the form of crystals
  8. filtrationIt is filtered off
  9. washwashed with absolute alcohol
  10. customAfter drying in vacuo, it melts at about 190° C. with decomposition

Sources & evidence

ORD record
ord-83438abaee7048399940198fbecf123e
Source dataset
uspto-grants-1979_04
Patent number
US04149848

Reaction notes

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