Ethyl Acetate → 2-(1,3-Dioxolan-2-yl)-4-methoxyaniline

HRID 709881Notes

Reaction equation

HRID 709881 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N+:14]([O-])=O)=[C:7]([CH:9]2[O:13][CH2:12][CH2:11][O:10]2)[CH:8]=1.C(OCC)(=O)C>[Pt](=O)=O.O.O.O.C([O-])(=O)C.[Na+]>[O:10]1[CH2:11][CH2:12][O:13][CH:9]1[C:7]1[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=1[NH2:14]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 572490272-(5-Methoxy-2-nitrophenyl)-1,3-dioxolane

Product 1

HCID 153389082-(1,3-Dioxolan-2-yl)-4-methoxyanilineYield 100%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 23665404Sodium Acetate TrihydrateCatalyst

Procedure

2-(5-Methoxy-2-nitrophenyl)-1,3-dioxolane (15.00 g, 0.06661 mol), platinum dioxide (900 mg, 0.004 mol) and sodium acetate trihydrate (700 mg, 0.005 mol) were placed in a pressure flask, followed by ethyl acetate (400 mL, 4 mol). The reaction mixture was then purged under N2 for at least 3 times, and H2 was introduced (purged 3 times) and maintained at 52 psi for 3 hours. The reaction mixture was then filtered, and solvent was removed to give a pure product (13 g, 100%). 1H NMR (CHLOROFORM-d) δ: 6.96 (d, J=2.8 Hz, 1H), 6.76 (dd, J=8.5, 3.0 Hz, 1H), 6.64 (d, J=8.5 Hz, 1H), 5.84 (s, 1H), 4.00-4.18 (m, 4H), 3.89 (br. s., 2H). MS (M+1): 196.10.

Workup

  1. customThe reaction mixture was then purged under N2 for at least 3 times, and H2
  2. additionwas introduced
  3. custom(purged 3 times)
  4. temperaturemaintained at 52 psi for 3 hours
  5. filtrationThe reaction mixture was then filtered
  6. customsolvent was removed

Sources & evidence

ORD record
ord-641fcc5050eb4cdabcd25a3f631d1a48
Source dataset
uspto-grants-2015_11
Patent number
US09181191B2

Reaction notes

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