Ammonium Chloride → HCID 21963679, compound

HRID 988953Notes

Reaction equation

HRID 988953 reaction equation
[CH2:1]([N:8]1[CH2:13][CH:12]2[CH2:14][CH:9]1[CH2:10][N:11]2[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N+:21]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH4+].[Cl-]>C(O)C.O.[Fe]>[CH2:1]([N:8]1[CH2:13][CH:12]2[CH2:14][CH:9]1[CH2:10][N:11]2[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[NH2:21])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 21963669HCID 21963669, compound

Product 1

HCID 21963679HCID 21963679, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

5.0 g (124) in 360 mL ethanol and 20 mL water with 4 g NH4Cl and 6.7 iron powder were heated to reflux temperature under 4 hours of mechanical agitation. The reaction solution is filtered over Celite and active carbon, evaporated, absorbed in 100 mL water, brought to pH 10 by means of K2CO3 and extracted with ether (4×50 mL). The combined organic phases were dried with Na2SO4, evaporated and distilled in a bulb tube (Kp: 5 mbar; 160-170° C.): 2.20 g (48.8% of the theoretical yield.) (125) as colorless oil. DC: CHCl3/methanol (9:1).

Workup

  1. temperatureto reflux temperature under 4 hours of mechanical agitation
  2. filtrationThe reaction solution is filtered over Celite and active carbon
  3. customevaporated
  4. customabsorbed in 100 mL water
  5. extractionextracted with ether (4×50 mL)
  6. dry with materialThe combined organic phases were dried with Na2SO4
  7. customevaporated
  8. distillationdistilled in a bulb tube (Kp: 5 mbar; 160-170° C.)

Sources & evidence

ORD record
ord-5a7783ee41b2430789d87a30b38a453a
Source dataset
uspto-grants-2003_10
Patent number
US06638925B2

Reaction notes

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