Ammonium Chloride → HCID 22258925, compound

HRID 1611126Notes

Reaction equation

HRID 1611126 reaction equation
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-])=O)[C:10]=2[C:18](=[O:20])[CH3:19])=[CH:5][CH:4]=1.[Cl-].[NH4+]>C(O)C.O.[Fe]>[NH2:15][C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([O:8][CH2:7][C:6]2[CH:21]=[CH:22][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:10]=1[C:18](=[O:20])[CH3:19]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 22258790HCID 22258790, compound

Product 1

HCID 22258925HCID 22258925, compoundYield 175.5%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred suspension of 1-{2-[(4-methoxybenzyl)oxy]-6-nitrophenyl}ethanone (0.50 g, 1.659 mmol) in ethanol was added a solution of ammonium chloride (0.10 g, 1.825 mmol) in water (5 mL) followed by iron powder (0.75 g). The mixture was stirred at 100° C. for 1 hr. The reaction mixture was filtrated on Celite®. The filtrate was diluted with ethyl acetate and washed with water. The separated organic phase was washed with brine and dried over Na2SO4, filtrated and concentrated under reduced pressure to give 1-{2-amino-6-[(4-methoxybenzyl)oxy]phenyl}ethanone as a yellow solid (0.790 g, yield; 108%). The residue was used for the next step without further purification. [Starting Compound 1I]

Workup

  1. filtrationThe reaction mixture was filtrated on Celite®
  2. additionThe filtrate was diluted with ethyl acetate
  3. washwashed with water
  4. washThe separated organic phase was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltrated
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-825d61235d3f41eb9283b21afb8a1797
Source dataset
uspto-grants-2006_01
Patent number
US06984649B1

Reaction notes

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