Ammonium Chloride → 2-Amino-5-methoxy-4-(2-propenyl)benzylalcohol

HRID 494948Notes

Reaction equation

HRID 494948 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:8]([N+:14]([O-])=O)=[CH:9][C:10]=1[CH2:11][CH:12]=[CH2:13])[CH2:6][OH:7].[Cl-].[NH4+]>[Fe].C(O)C.O>[NH2:14][C:8]1[CH:9]=[C:10]([CH2:11][CH:12]=[CH2:13])[C:3]([O:2][CH3:1])=[CH:4][C:5]=1[CH2:6][OH:7]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 576827814-Allyl-5-methoxy-2-nitrobenzyl alcohol

Product 1

HCID 576828172-Amino-5-methoxy-4-(2-propenyl)benzylalcoholYield 91.6%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Conditions

Temperature
90 °C

Procedure

24 ml of ethanol-water (5:1) was added to 1.00 g of 3-methoxy-6-nitro-4-(2-propenyl)benzylalcohol, 1.00 g of iron, and 2.00 g of ammonium chloride. The reaction solution was stirred at 90° C. for 1 hour. Thereafter, the reaction solution was cooled to a room temperature, and insoluble matters were then removed by filtration. The filtrate was concentrated under a reduced pressure. The residue was diluted with ethyl acetate and then washed with water and a saturated sodium chloride aqueous solution. The organic layer was dried over magnesium sulfate and then concentrated under a reduced pressure, so as to obtain 793 mg of the subject compound.

Workup

  1. temperatureThereafter, the reaction solution was cooled to a room temperature
  2. custominsoluble matters were then removed by filtration
  3. concentrationThe filtrate was concentrated under a reduced pressure
  4. additionThe residue was diluted with ethyl acetate
  5. washwashed with water
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. concentrationconcentrated under a reduced pressure

Sources & evidence

ORD record
ord-c3f847be2293478280ea600e498627a4
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

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