Acetic Acid → HCID 18315076, compound

HRID 1421471Notes

Reaction equation

HRID 1421471 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[C:7]2[C:3]=1[CH:4]=[C:5]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[NH:6]2.C(O)(=O)C>[Fe].O>[NH2:11][C:8]1[CH:9]=[CH:10][C:2]([Cl:1])=[C:3]2[C:7]=1[NH:6][C:5]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:4]2

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 18315077HCID 18315077, compound

Product 1

HCID 18315076HCID 18315076, compoundYield 16.8%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent2×

Conditions

Temperature
25 °C

Procedure

A stirred solution of 2.68 grams (0.01 mole) of 4-chloro-2-ethoxycarbonyl-7-nitroindole, 80 mL of acetic acid, and 15 mL of water was heated to 65° C., and 18.3 grams (0.048 mole) of iron powder was slowly added during a 20 minute period. Upon completion of addition, the reaction mixture was allowed to cool to 25° C. where it stirred for one hour. After this time, the reaction mixture was poured into water, and the resulting mixture was filtered through diatomaceous earth. The filter cake was washed thoroughly with ethyl acetate. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure a residue. The residue was purified by column chromatography, yielding 0.4 gram of title compound. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of addition
  2. filtrationthe resulting mixture was filtered through diatomaceous earth
  3. washThe filter cake was washed thoroughly with ethyl acetate
  4. dry with materialThe organic layer was dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure a residue
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-7afa38cc474f46e193a03a675b1f2d21
Source dataset
uspto-grants-2000_06
Patent number
US06077812

Reaction notes

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