HCID 14940799, compound → 3-Aminophenyl 2,2-dimethylpropanoate

HRID 1938452Notes

Reaction equation

HRID 1938452 reaction equation
[C:1]([O:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-])=O)[CH:9]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]>[Pd].C(Cl)Cl>[C:1]([O:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([NH2:14])[CH:9]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

4

Reactant 1

HCID 14940799HCID 14940799, compound

Product 1

HCID 118302903-Aminophenyl 2,2-dimethylpropanoateYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

To 60 mL anhydrous CH2Cl2 was added O-pivaloyl-3-nitrophenol (5.0 g, 22.4 mmol) and a catalytic amount (50 mg) of 10% Pd on C. The flask was repeatedly evacuated and flushed with N2. The reaction flask was again evacuated and H2 was introduced by balloon. After stirring under an atmosphere of H2 for 3 h, the reaction flask was flushed twice with N2. The suspension was then filtered through a bed of Celite™ and concentrated to give 4.15g (96%) of O-pivaloyl-3-aminophenol as a viscous amber oil. Data for O-pivaloyl-3-aminophenol: Rf 0.21 (silica gel, hexanes/EtOAc, 3:1); 1H NMR (400 MHz, CDCl3) 7.12 (dd, J=8.0, 8.0, 1H), 6.52 (dd, J=7.8, 2.7, 1H), 6.44 (ddd, J=8.0, 2.4, 1.4, 1H), 6.38 (t, J=2.2, 1H), 3.81 (br s, 2H), 1.34 (s, 9H).

Workup

  1. customThe flask was repeatedly evacuated
  2. customflushed with N2
  3. customThe reaction flask was again evacuated
  4. additionH2 was introduced by balloon
  5. customthe reaction flask was flushed twice with N2
  6. filtrationThe suspension was then filtered through a bed of Celite™
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c4c0be3fd7154c70b3628fef16198453
Source dataset
uspto-grants-1997_12
Patent number
US05693647

Reaction notes

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