Ammonium Chloride → HCID 21959409, compound

HRID 887566Notes

Reaction equation

HRID 887566 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][C:6]=1[C:14]1[CH:19]=[CH:18][N+:17]([CH3:20])=[CH:16][CH:15]=1)([CH3:4])([CH3:3])[CH3:2].[NH4+].[Cl-].[BH4-].[Na+]>O.CCO.C(Cl)Cl.[Fe]>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][C:6]=1[C:14]1[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH:15]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydride2×HCID 21959481HCID 21959481, compound

Product 1

HCID 21959409HCID 21959409, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 6344DichloromethaneSolventHCID 19096565Water ethanolSolvent

Procedure

4-(2-tert-Butyl-5-nitrophenyl)-1-methylpyridinium (2.1 g, 7.8 mmol, Step C) was added to a 100 mL round-bottom flask and dissolved in a 10% H2O/EtOH mixture. To the flask iron dust (1.31 g, 23.4 mmol, 3 eq) and NH4Cl (460 mg, 8.6 mmol, 1.1 eq) were added. The flask was placed in a 100° C. sand bath and heated to reflux. After 2 h, the solution was cooled to RT and filtered through a pad of Celite®. The resulting solution was stripped down to a yellow solid and redissolved in MeOH (20 mL, anhydrous). The solution was cooled to 0° C. by placing it in an ice bath and slowly adding NaBH4 (450 mg, 11.7 mmol, 1.5 eq). After addition of the NaBH4, the solution was cooled to RT and stirred for 30 min. The solvent was stripped-off under vacuum and the solid was redissolved in CH2Cl2 and filtered. The solution was concentrated in vacuo to afford an amorphous clear yellow solid. MS (ES+): 245.2 (M+H)+. Calc'd for C16H24N2: 244.2.

Workup

  1. customwas placed in a 100° C.
  2. temperatureheated to reflux
  3. filtrationfiltered through a pad of Celite®
  4. dissolutionredissolved in MeOH (20 mL, anhydrous)
  5. temperatureThe solution was cooled to 0° C.
  6. temperaturethe solution was cooled to RT
  7. filtrationfiltered
  8. concentrationThe solution was concentrated in vacuo
  9. customto afford an amorphous clear yellow solid

Sources & evidence

ORD record
ord-a3f1d399142846c095422d5d0f1b9e0b
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

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