Ammonium Chloride → 2-methyl-4-amino-N-tetrahydrofurfurylaniline dihydrochloride monohydrate

HRID 26340Notes

Reaction equation

HRID 26340 reaction equation
[Cl-:1].[NH4+].[CH3:3][C:4]1[CH:16]=[C:15]([N+:17]([O-])=O)[CH:14]=[CH:13][C:5]=1[NH:6][CH2:7][CH:8]1[O:12][CH2:11][CH2:10][CH2:9]1>[Zn]>[OH2:12].[ClH:1].[ClH:1].[CH3:3][C:4]1[CH:16]=[C:15]([NH2:17])[CH:14]=[CH:13][C:5]=1[NH:6][CH2:7][CH:8]1[O:12][CH2:11][CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 226105972-methyl-4-nitro-N-tetrahydrofurfurylaniline

Product 1

HCID 213228052-methyl-4-amino-N-tetrahydrofurfurylaniline dihydrochloride monohydrate

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

5 g of ammonium chloride and 83 g of zinc powder are added to 250 ml of an aqueous-alcoholic solution (85% of alcohol and 15% of water). This mixture is heated to the reflux temperature, whilst stirring, and 0.168 mol (39.8 g) of 2-methyl-4-nitro-N-tetrahydrofurfurylaniline is then added gradually. When the addition of the nitro derivative has ended and the reaction medium is completely decolorised, the latter is filtered and the filtrate is collected in 40 ml of ice-cooled hydrochloric acid (d=1.19). 80 ml of acetone are added to the filtrate. 2-Methyl-4-amino-N-tetrahydrofurfurylaniline dihydrochloride precipitates in the form of the monohydrate. The crystalline product is filtered off and washed with absolute alcohol and then acetone. After drying in vacuo, it melts at about 210° C. with decomposition.

Workup

  1. temperatureThis mixture is heated to the reflux temperature
  2. filtrationthe latter is filtered
  3. customthe filtrate is collected in 40 ml of ice-
  4. temperaturecooled hydrochloric acid (d=1.19)
  5. addition80 ml of acetone are added to the filtrate
  6. custom2-Methyl-4-amino-N-tetrahydrofurfurylaniline dihydrochloride precipitates in the form of the monohydrate
  7. filtrationThe crystalline product is filtered off
  8. washwashed with absolute alcohol
  9. customAfter drying in vacuo, it melts at about 210° C. with decomposition

Sources & evidence

ORD record
ord-adbbed078b494ba3ba30377556bc3e35
Source dataset
uspto-grants-1979_04
Patent number
US04149848

Reaction notes

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