Hydrazine → HCID 22144524, compound

HRID 1824783Notes

Reaction equation

HRID 1824783 reaction equation
[Cl:1][C:2]1[C:3]([N+:11]([O-])=O)=[C:4]([OH:10])[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1.NN>CCO.C(OCC)(=O)C.[Ru]>[NH2:11][C:3]1[C:2]([Cl:1])=[CH:7][C:6]([O:8][CH3:9])=[CH:5][C:4]=1[OH:10]

Participants

6

Reactant 2

HCID 9321HydrazineHCID 22144507HCID 22144507, compound2×

Product 1

HCID 22144524HCID 22144524, compoundYield 76%

Reagents, catalysts & solvents 3

HCID 23950RutheniumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

To 3-chloro-5-methoxy-2-nitrophenol, synthetic method A [1], (200 mg) in 95% EtOH (10 mL) was added 5% Ru/C (20 mg) and hydrazine (0.36 mL). The mixture was placed in an oil bath and heated to 85° C. for 2 h. After reaction cooled, the mixture was diluted with ethyl acetate and filtered through a pad of celite and concentrated. Flash chromatography on silica gel eluting with 30% ethyl acetate-hexane afforded 138 mg (76%) of the title compound as a solid. MS: 174 (MH+), HPLC tR: 0.84 min.

Workup

  1. customThe mixture was placed in an oil bath
  2. customAfter reaction
  3. temperaturecooled
  4. filtrationfiltered through a pad of celite
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-73d1444d498b4317bd72e1d820d76682
Source dataset
uspto-grants-2006_05
Patent number
US07045539B2

Reaction notes

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