Acetic Acid → 4-Chloro-3-methoxyaniline

HRID 1722053Notes

Reaction equation

HRID 1722053 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[O:11][CH3:12].C(O)(=O)C.CCOCC>C(O)C.Cl.[Fe]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[O:11][CH3:12]

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 3283Diethyl EtherHCID 705192-Chloro-5-nitroanisole

Product 1

HCID 131036924-Chloro-3-methoxyaniline

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalyst2×HCID 23925IronCatalyst2×HCID 702EthanolSolvent

Procedure

2-Chloro-5-nitroanisol (10 g, 0.053 mol), iron powder (15 g, 0.26 mol) and glacial acetic acid (20 ml, 0.355 mol) were combined in 125 ml ethanol. Concentrated HCl (2 drops) was added and the mixture refluxed 2 hours. Additional iron powder (5 g) and concentrated HCl (1 drop) were added and reflux continued for an additional 16 hours. The reaction mixture was cooled, poured into equal volumes each of ice/water and ether, filtered and the layers separated. The aqueous layer was extracted with fresh ether and the combined ether layers extracted with 1N HCl. The original aqueous and 1N HCl extract were combined, the pH adjusted to 6 with saturated Na2CO3 and extracted with fresh ether. The last ether extract was dried over MgSO4 and stripped to yield title product, 82 g, m.p. 77°-79° C.

Workup

  1. temperaturethe mixture refluxed 2 hours
  2. temperaturereflux
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. customthe layers separated
  6. extractionThe aqueous layer was extracted with fresh ether
  7. extractionthe combined ether layers extracted with 1N HCl
  8. extractionThe original aqueous and 1N HCl extract
  9. extractionextracted with fresh ether
  10. extractionThe last ether extract
  11. dry with materialwas dried over MgSO4

Sources & evidence

ORD record
ord-3a4afc2ee63145729ecc4ac85b52cf60
Source dataset
uspto-grants-1989_08
Patent number
US04853410

Reaction notes

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