Sulfuric Acid → 3-[Methyl-(4-nitro-phenyl)-amino]-propionic acid

HRID 37835Notes

Reaction equation

HRID 37835 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][CH:4]=1.[C:12]([OH:16])(=[O:15])[CH:13]=[CH2:14].S(=O)(=O)(O)O>O>[CH3:1][N:2]([C:3]1[CH:4]=[CH:5][C:6]([N+:9]([O-:11])=[O:10])=[CH:7][CH:8]=1)[CH2:14][CH2:13][C:12]([OH:16])=[O:15]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6581Acrylic AcidHCID 7483N-Methyl-4-nitroaniline

Product 1

HCID 112530753-[Methyl-(4-nitro-phenyl)-amino]-propionic acidYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
80 °C

Procedure

Methyl-(4-nitro-phenyl)-amine (3.0 g, 19.7 mmol) and acrylic acid (4.06 mL, 59.2 mmol) were added at 0° C. to a solution of concentrated sulfuric acid (2.15 mL, 39.5 mmol) in water (28 mL). The reaction mixture was heated at 80° C. for 30 min, cooled to room temperature and diluted with water. The precipitated solid was filtered and dried to give a crude product which was purified by washing with diethyl ether and pentane, affording 3-[methyl-(4-nitro-phenyl)-amino]-propionic acid (4.0 g, 91%) as a yellow solid.

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe precipitated solid was filtered
  3. customdried
  4. customto give a crude product which
  5. customwas purified
  6. washby washing with diethyl ether and pentane

Sources & evidence

ORD record
ord-c6d8aeeb84454920896084ab93b226f0
Source dataset
uspto-grants-2013_09
Patent number
US08524705B2

Reaction notes

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