Potassium Carbonate → 3-Methoxy-4-nitroaniline

HRID 1773557Notes

Reaction equation

HRID 1773557 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:12]C(=O)C)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10].C(=O)([O-])[O-].[K+].[K+]>Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH2:12])[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 13734467N-(3-Methoxy-4-nitrophenyl)acetamide

Product 1

HCID 27557953-Methoxy-4-nitroanilineYield 102.5%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of N-(3-methoxy-4-nitro-phenyl)-acetamide (16.6 g, 78.67 mmol) and an aqueous solution of hydrochloric acid (1.5 M, 200 mL) was refluxed until a clear solution was obtained. The reaction mixture was basified by addition of an aqueous solution of potassium carbonate and then was extracted four times with dichloromethane (200 mL); the combined organic extracts were dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to give 13.56 g (quantitative yield) of 3-methoxy-4-nitro-phenylamine as a yellow solid. MS=169 [M+H]+.

Workup

  1. customwas obtained
  2. extractionwas extracted four times with dichloromethane (200 mL)
  3. dry with materialthe combined organic extracts were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-ac32929e6bcd4527ae67a65748c8fc93
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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