Methylhydroquinone → HCID 18461463, compound

HRID 2303876Notes

Reaction equation

HRID 2303876 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:5]=1[OH:6].Cl[C:13]1[CH:14]=[CH:15][C:16]([N+:28]([O-:30])=[O:29])=[C:17]([N:19]([CH3:27])[C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH:18]=1>CN(C)C=O>[OH:11][C:9]1[CH:8]=[CH:7][C:5]([O:6][C:13]2[CH:14]=[CH:15][C:16]([N+:28]([O-:30])=[O:29])=[C:17]([N:19]([CH3:27])[C:20](=[O:26])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[CH:18]=2)=[C:4]([CH3:3])[CH:10]=1

Participants

5

Reactant 3

HCID 7253MethylhydroquinoneHCID 24758Sodium hydrideHCID 15544598tert-butyl N-(5-chloro-2-nitrophenyl)-N-methylcarbamate

Product 1

HCID 18461463HCID 18461463, compoundYield 58.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (55 wt. %, 0.87 g) in N,N-dimethylformamide (20 ml) was added methylhydroquinone (1.24 g). The mixture was stirred at ambient temperature for 15 minutes. To this mixture was added t-butyl N-(5-chloro-2-nitrophenyl)-N-methylcarbamate (2.87 g)in small portions and stirred at 120° C. for 2 hours. The reaction mixture was concentrated and the residue was partitioned between ethyl acetate and water. The ethyl acetate layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using n-hexane/ethyl acetate=3/1 as the eluant to afford a mixture (2.20 g) of t-butyl N-[5-(4-hydroxy-2-methylphenoxy)-2-nitrophenyl]-N-methylcarbamate and t-butyl N-[5-(4-hydroxy-3-methylphenoxy)-2-nitrophenyl]-N-methylcarbamate. A mixture of a solution of the above product and palladium on carbon (10%, 0.21 g) was vigorously stirred at ambient temperature under hydrogen atmosphere for 2 hours. At the end of this time the catalyst was removed by filtration and the filtrate was concentrated to give the title compound (1.88 g).

Workup

  1. stirringstirred at 120° C. for 2 hours
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was partitioned between ethyl acetate and water
  4. dry with materialThe ethyl acetate layer was dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-d36efa73882d4c1eb1923eebcea6fa8c
Source dataset
uspto-grants-2002_08
Patent number
US06432993B1

Reaction notes

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