Water → HCID 59395069, compound

HRID 383390Notes

Reaction equation

HRID 383390 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)[C:5]([O:13][CH3:14])=[CH:4][C:3]=1[N+:15]([O-])=O.O>C(O)(=O)C.C(OCC)(=O)C.[Zn]>[Br:1][C:2]1[CH:7]=[C:6]([CH:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)[C:5]([O:13][CH3:14])=[CH:4][C:3]=1[NH2:15]

Participants

6

Reactant 2

HCID 962WaterHCID 59394935HCID 59394935, compound

Product 1

HCID 59395069HCID 59395069, compoundYield 95.3%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-Bromo-5-cyclopentyl-4-methoxy-2-nitrobenzene (100 mg, 0.33 mmol) was dissolved in acetic acid (1 mL) and water (250 μL) and treated with Zn (109 mg, 1.67 mmol) at room temperature and stirred for 1.5 h. The reaction was diluted with ethyl acetate and filtered. The organic layer was washed with 50% saturated NaHCO3 and brine, dried over Na2SO4, filtered, and concentrated in vacuo to provide 2-bromo-4-cyclopentyl-5-methoxyaniline as a clear brown oil (85 mg, 94% yield). LC/MS m/z 270.2 [M+H]+.

Workup

  1. filtrationfiltered
  2. washThe organic layer was washed with 50% saturated NaHCO3 and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fd0a618905fb46be93b62a64f3130e52
Source dataset
uspto-grants-2013_02
Patent number
US08367660B2

Reaction notes

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