tert-Butyl 3-methyl-4-nitrobenzoate → tert-Butyl 4-amino-3-methylbenzoate

HRID 1893538Notes

Reaction equation

HRID 1893538 reaction equation
[C:1]([O:5][C:6](=[O:17])[C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[C:9]([CH3:16])[CH:8]=1)([CH3:4])([CH3:3])[CH3:2]>C(O)C.O1CCCC1.[C].[Pd]>[C:1]([O:5][C:6](=[O:17])[C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[C:9]([CH3:16])[CH:8]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 1

HCID 15283350tert-Butyl 3-methyl-4-nitrobenzoate

Product 1

HCID 53432587tert-Butyl 4-amino-3-methylbenzoateYield 106.2%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

The compound (55.6 g, 234 mmol) obtained in step A was dissolved in an ethanol (200 ml)-tetrahydrofuran (100 ml) mixed solvent. Then, 10% palladium carbon (containing water) (10 g) suspended in ethanol (20 ml) was added. Under a hydrogen atmosphere and at room temperature, the reaction mixture was stirred for 5 hr, and filtered off through celite. The obtained solution was concentrated under reduced pressure to give the title compound (51.5 g) as a bistered oil.

Workup

  1. additionmixed solvent
  2. additionwas added
  3. filtrationfiltered off through celite
  4. concentrationThe obtained solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0e78d576db5141ff8e8ff2c5e463b656
Source dataset
uspto-grants-2013_08
Patent number
US08513235B2

Reaction notes

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