Ammonium Chloride → HCID 23130624, compound

HRID 2080172Notes

Reaction equation

HRID 2080172 reaction equation
[NH2:1][C:2]1[N:28]=[CH:27][CH:26]=[CH:25][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[N+:22]([O-])=O)=[CH:10][CH:9]=1)=[O:5].[Cl-].[NH4+]>C(O)C.O1CCCC1.O.[Fe]>[NH2:1][C:2]1[N:28]=[CH:27][CH:26]=[CH:25][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[NH2:22])=[CH:10][CH:9]=1)=[O:5]

Participants

5

Reactant 2

HCID 25517Ammonium Chloride2×HCID 23130557HCID 23130557, compound

Product 1

HCID 23130624HCID 23130624, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 23925IronCatalyst2×HCID 18504229Ethanol tetrahydrofuran waterSolvent

Procedure

2-Amino-N-(4-(2-nitrobenzyloxy)-benzyl)-nicotinamide described in Example A-15 was dissolved in a mixture solvent of ethanol-tetrahydrofuran-water (3:1:1.5), iron powder (4 mg) and ammonium chloride (85 mg) were added thereto, and the solution was stirred overnight under reflux. In addition, iron powder (10 mg) and ammonium chloride (20 mg) were added, and the solution was stirred under reflux for 2 hours. The reaction solution was allowed to room temperature, filtered through Celite pad to remove insoluble matter, and the filtrate was concentrated in vacuo. The residue was purified by NH silica gel chromatography (hexane:ethyl acetate), and the title compound (9 mg, 98%) was obtained as a pale brown solid.

Workup

  1. additionwere added
  2. temperatureunder reflux
  3. stirringthe solution was stirred
  4. temperatureunder reflux for 2 hours
  5. customwas allowed to room temperature
  6. filtrationfiltered through Celite pad
  7. customto remove insoluble matter
  8. concentrationthe filtrate was concentrated in vacuo
  9. customThe residue was purified by NH silica gel chromatography (hexane:ethyl acetate)

Sources & evidence

ORD record
ord-da23e646e3144c28a647967e38227b9e
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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