Ammonium Chloride → HCID 86661625, compound

HRID 1843688Notes

Reaction equation

HRID 1843688 reaction equation
[CH3:1][O:2][C:3]1[CH:28]=[CH:27][C:6]([CH2:7][O:8][C:9]2[CH:10]=[CH:11][C:12]([N+:24]([O-])=O)=[C:13]([CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:14]=2)=[CH:5][CH:4]=1.[Cl-].[NH4+]>C(O)C.O.[Fe]>[NH2:24][C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:7][C:6]2[CH:27]=[CH:28][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:14][C:13]=1[CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:21])([CH3:20])[CH3:22]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 86661624HCID 86661624, compound

Product 1

HCID 86661625HCID 86661625, compoundYield 100.1%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of tert-butyl {5-[(4-methoxybenzyl)oxy]-2-nitrophenyl}methylcarbamate produced in Example (1a) (209 g, 538 mmol), iron powder (150 g, 2.69 mol) and ammonium chloride (15.0 g, 280 mmol) in ethanol (1.2 L) and water (1 L) was stirred with heating under reflux for five hours. After leaving to cool, the reaction mixture was filtered through celite. The filtrate was concentrated to about half volume under reduced pressure, and the concentrated residue was extracted with toluene (1 L) twice. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the title compound (193 g, 99%) as a brown oil.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for five hours
  3. customAfter leaving
  4. temperatureto cool
  5. filtrationthe reaction mixture was filtered through celite
  6. concentrationThe filtrate was concentrated to about half volume under reduced pressure
  7. extractionthe concentrated residue was extracted with toluene (1 L) twice
  8. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d08a9a9e010a46e1993e25678f1db2ed
Source dataset
uspto-grants-2015_02
Patent number
US08946264B2

Reaction notes

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