HCID 86631944, compound → HCID 86631945, compound

HRID 906136Notes

Reaction equation

HRID 906136 reaction equation
[CH3:1][C:2]1[C:14]([N+:15]([O-])=O)=[C:13]([C:18]([O:20][CH3:21])=[O:19])[C:12]([CH3:22])=[CH:11][C:3]=1[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].[H][H]>O1CCCC1.[Pd]>[NH2:15][C:14]1[C:2]([CH3:1])=[C:3]([CH:11]=[C:12]([CH3:22])[C:13]=1[C:18]([O:20][CH3:21])=[O:19])[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5]

Participants

5

Reactant 2

HCID 86631944HCID 86631944, compoundHCID 178418361HCID 178418361, compound3×

Product 1

HCID 86631945HCID 86631945, compoundYield 98.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst3×HCID 8028TetrahydrofuranSolvent

Procedure

1-tert-Butyl 4-methyl 2,5-dimethyl-3-nitroterephthalate (0.5 g, 1.62 mmol) was dissolved in tetrahydrofuran (4 mL). 10 wt % Palladium on carbon (Degussa type, 50 mg) was added to the solution and the mixture was treated with hydrogen at ambient temperature for 3 h. 10 wt % Palladium on carbon (Degussa type, 50 mg) was added to the solution, and the mixture was treated with hydrogen at ambient temperature for a further 2 h. 10 wt % Palladium on carbon (Degussa type, 100 mg) was added to the solution, and the mixture was treated with hydrogen at ambient temperature for a further 5 h. The mixture was filtered and the filtrate was concentrated to afford 1-tert-butyl 4-methyl 3-amino-2,5-dimethylterephthalate (0.444 g, 1.59 mmol, 98% yield) as a brown oil. 1H NMR (400 MHz, CDCl3): δ 6.78 (s, 1H), 5.20 (br s, 2H), 3.90 (s, 3H), 2.40 (s, 3H), 2.24 (s, 3H), 1.59 (s, 9H); MS (EI) for C15H21NO4: 280 (MH+).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-ee6c0f76a856459ba603b2870b1b560b
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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