Dichloromethane → HCID 19417510, compound

HRID 864969Notes

Reaction equation

HRID 864969 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][CH2:12][C:13]1[CH:14]=[C:15]([N+:19]([O-])=O)[CH:16]=[CH:17][CH:18]=1.C(Cl)[Cl:23]>O.C(O)(=O)C.[Fe]>[ClH:23].[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][CH2:12][C:13]1[CH:14]=[C:15]([CH:16]=[CH:17][CH:18]=1)[NH2:19]

Participants

6

Reactant 2

HCID 6344DichloromethaneHCID 894627HCID 894627, compound

Product 1

HCID 19417510HCID 19417510, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Under a nitrogen atmosphere, a stirred mixture of 4.5 grams (0.016 mole) 3-(naphth-2-yloxymethyl)nitrobenzene and 4.5 grams (0.081 mole) of iron powder in 10 mL of water and 50 mL of acetic acid was heated at reflux for about six hours. After this time the reaction mixture was cooled to ambient temperature, and 100 mL of methylene chloride was added. The mixture was filtered, and an additional 100 mL of methylene chloride was added to the filtrate. The methylene chloride layer was separated and washed with four portions of an aqueous solution saturated with sodium bicarbonate and then with two portions of an aqueous solution saturated with sodium chloride. The organic layer was dried with magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure to a residue. The residue was then dissolved in diethyl ether and treated with an excess of an ethereal solution of hydrogen chloride. The resultant precipitate was collected by filtration and recrystallized from ethyl acetate and diethyl ether, yielding 3.1 grams of 3-(naphth-2-yloxymethyl)aniline hydrochloride. The NMR spectrum was consistent with the proposed structure.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for about six hours
  3. filtrationThe mixture was filtered
  4. additionan additional 100 mL of methylene chloride was added to the filtrate
  5. customThe methylene chloride layer was separated
  6. washwashed with four portions of an aqueous solution saturated with sodium bicarbonate
  7. dry with materialThe organic layer was dried with magnesium sulfate
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated under reduced pressure to a residue
  10. dissolutionThe residue was then dissolved in diethyl ether
  11. additiontreated with an excess of an ethereal solution of hydrogen chloride
  12. filtrationThe resultant precipitate was collected by filtration
  13. customrecrystallized from ethyl acetate and diethyl ether

Sources & evidence

ORD record
ord-7d6b690f529b4bb1acaca0a6f6a2f2bc
Source dataset
uspto-grants-1996_10
Patent number
US05565451

Reaction notes

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