HCID 18321632, compound → 1,1-Dimethylethyl 3-amino-α,α-dimethylbenzeneacetate

HRID 1698776Notes

Reaction equation

HRID 1698776 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]([CH3:19])([CH3:18])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-])=O>C(O)C.[C].[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([C:10]([CH3:19])([CH3:18])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 18321632HCID 18321632, compound

Product 1

HCID 183216371,1-Dimethylethyl 3-amino-α,α-dimethylbenzeneacetateYield 89.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of t-butyl 2-(3-nitrophenyl)-2-methyl-propionate (3.6 g) in ethanol (100 mL), 10% palladium carbon (400 mg) was added, followed by stirring at room temperature for 2 hours under a hydrogen atmosphere. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate: n-hexane=1:5), whereby tert-butyl 2-(3-aminophenyl)-2-methylpropionate (2.87 g) was obtained.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate: n-hexane=1:5)

Sources & evidence

ORD record
ord-9edf6184d24249bbbd94b93b1e986355
Source dataset
uspto-grants-2002_02
Patent number
US06344452B1

Reaction notes

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