Methyl 2,2-dimethyl-3-(4-nitrophenyl)propanoate → Methyl 3-(4-aminophenyl)-2,2-dimethyl-propanoate

HRID 2174210Notes

Reaction equation

HRID 2174210 reaction equation
[CH3:1][C:2]([CH3:17])([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=1)[C:3]([O:5][CH3:6])=[O:4]>CO>[NH2:14][C:11]1[CH:10]=[CH:9][C:8]([CH2:7][C:2]([CH3:17])([CH3:1])[C:3]([O:5][CH3:6])=[O:4])=[CH:13][CH:12]=1

Participants

3

Reactant 1

HCID 77230590Methyl 2,2-dimethyl-3-(4-nitrophenyl)propanoate

Product 1

HCID 89650896Methyl 3-(4-aminophenyl)-2,2-dimethyl-propanoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound (i) (736 mg, 3.06 mmol) was dissolved in MeOH (15 mL) at RT and this solution degassed with N2. Palladium on carbon (10%) (25 mg) was suspended in water/MeOH (0.5 mL/2 mL) and added to the substrate solution. The mixture was again degassed with N2 and then vacuum/flushed with H2. The mixture was stirred under a H2 balloon overnight at RT. The mixture was filtered through celite, washed with MeOH and the filtrate evaporated to dryness to afford a clear oil which was placed under high vacuum for 1 h to afford the desired product (ii), 620 mg. 1H NMR (400 MHz, CDCl3) δ 6.88 (d, J=8.3 Hz, 2H), 6.60 (d, J=8.3 Hz, 2H), 3.64 (s, 3H), 2.74 (s, 2H), 1.15 (s, 6H).

Workup

  1. customthis solution degassed with N2
  2. additionadded to the substrate solution
  3. customThe mixture was again degassed with N2
  4. customvacuum/flushed with H2
  5. filtrationThe mixture was filtered through celite
  6. washwashed with MeOH
  7. customthe filtrate evaporated to dryness
  8. customto afford a clear oil which
  9. waitwas placed under high vacuum for 1 h

Sources & evidence

ORD record
ord-6dbf6eea51b64b9597347acee36a325b
Source dataset
uspto-grants-2015_06
Patent number
US09060515B2

Reaction notes

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