4-Pentylphenyl 3-methyl-4-nitrobenzoate → 4-Pentylphenyl 4-amino-3-methylbenzoate

HRID 555196Notes

Reaction equation

HRID 555196 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[N+:22]([O-])=O)[C:5]([O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:10][CH:9]=1)=[O:6]>C(OCC)(=O)C.[Pd]>[NH2:22][C:21]1[CH:20]=[CH:19][C:4]([C:5]([O:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:10][CH:9]=2)=[O:6])=[CH:3][C:2]=1[CH3:1]

Participants

4

Reactant 1

HCID 129945594-Pentylphenyl 3-methyl-4-nitrobenzoate

Product 1

HCID 129945604-Pentylphenyl 4-amino-3-methylbenzoateYield 98.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

16.2 g of 4-pentylphenyl 3-methyl-4-nitrobenzoate (49.5 mM) were dissolved in 250 ml of ethyl acetate and 1.5 g of Pd/C (10%) were added. This mixture was hydrogenated at normal pressure. When the theoretical amount of hydrogen was consumed, it was filtered through a pad of celite filter aid and evaporated to dryness to give 14.5 g (49.0 mM, 98%) of 4-pentylphenyl 4-amino-3-methylbenzoate as beige crystals.

Workup

  1. customWhen the theoretical amount of hydrogen was consumed
  2. filtrationit was filtered through a pad of celite
  3. filtrationfilter aid
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-b42014e175704dc6b6e1048156452226
Source dataset
uspto-grants-2011_11
Patent number
US08053039B2

Reaction notes

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