4-Chloro-2,3-dihydro-2,2-dimethyl-7-nitrobenzofuran → 7-Amino-4-chloro-2,3-dihydro-2,2-dimethylbenzofuran

HRID 440653Notes

Reaction equation

HRID 440653 reaction equation
[Cl:1][C:2]1[C:7]2[CH2:8][C:9]([CH3:12])([CH3:11])[O:10][C:6]=2[C:5]([N+:13]([O-])=O)=[CH:4][CH:3]=1>C(O)(=O)C.O.[Fe]>[NH2:13][C:5]1[C:6]2[O:10][C:9]([CH3:11])([CH3:12])[CH2:8][C:7]=2[C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

5

Reactant 1

HCID 224047764-Chloro-2,3-dihydro-2,2-dimethyl-7-nitrobenzofuran

Product 1

HCID 224047737-Amino-4-chloro-2,3-dihydro-2,2-dimethylbenzofuranYield 68.9%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
50 °C

Procedure

A solution of 4.0 g (0.018 mole) of 4-chloro-2,3-dihydro-2,2-dimethyl-7-nitrobenzofuran in approximately 60 mL of glacial acetic acid was heated to 50° C. To this solution were added 10 mL of water, and, while maintaining the temperature at 50° C., 4.0 g (0.072 mole) of powdered iron. Upon completion of addition, the reaction mixture was allowed to cool to room temperature at which it stirred for an hour. Then the reaction mixture was diluted with 100 mL of water and filtered. The filtrate was extracted with diethyl ether, and the combined extracts were dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated from this filtrate under reduced pressure, leaving 2.45 g of 7-amino-4-chloro-2,3-dihydro-2,2-dimethylbenzofuran as a residue.

Workup

  1. additionUpon completion of addition
  2. temperatureto cool to room temperature at which it
  3. filtrationfiltered
  4. extractionThe filtrate was extracted with diethyl ether
  5. dry with materialthe combined extracts were dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customThe solvent was evaporated from this filtrate under reduced pressure

Sources & evidence

ORD record
ord-8324d1a6e5fe4377b4603c87d7f3917a
Source dataset
uspto-grants-1996_05
Patent number
US05521147

Reaction notes

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