Ammonium Chloride → 3-ethoxy-4-methylaniline

HRID 1505368Notes

Reaction equation

HRID 1505368 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[O:11][CH2:12][CH3:13].C1COCC1.O.[Cl-].[NH4+]>[Fe].O>[CH2:12]([O:11][C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][C:2]=1[CH3:1])[NH2:8])[CH3:13]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 21881883Oxolane--water (1/1)HCID 58897277HCID 58897277, compound2×

Product 1

HCID 2963233-ethoxy-4-methylanilineYield 91.9%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

Fe powder (609 mg, 10.90 mmol) was added to a solution of ethyl 2-methyl-5-nitrophenyl ether (Intermediate 88, 395 mg) in a mixture THF/water (15 mL/5 mL) followed by ammonium chloride (583 mg, 10.90 mmol). The reaction mixture was stirred overnight under nitrogen. The reaction mixture was poured into water (20 mL) and the iron was filtrated. Ethyl acetate was used to wash the solid filtrated. The filtrate was extracted with ethyl acetate (3 times). The combined ethyl acetate layers were dried over sodium sulphate and concentrated to give the title compound (303 mg) which was directly used in the next step.

Workup

  1. filtrationthe iron was filtrated
  2. washto wash the solid
  3. filtrationfiltrated
  4. extractionThe filtrate was extracted with ethyl acetate (3 times)
  5. dry with materialThe combined ethyl acetate layers were dried over sodium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c24a8635e23a494c82c642d8b8d47723
Source dataset
uspto-grants-2015_12
Patent number
US09216967B2

Reaction notes

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