HCID 58481111, compound → HCID 58481143, compound

HRID 1625699Notes

Reaction equation

HRID 1625699 reaction equation
[C:1]([C:4]1[CH:16]=[CH:15][C:7]([O:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][C:5]=1[N+:17]([O-])=O)(=[O:3])[CH3:2]>CO.[Pd]>[C:1]([C:4]1[CH:16]=[CH:15][C:7]([O:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][C:5]=1[NH2:17])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 58481111HCID 58481111, compound

Product 1

HCID 58481143HCID 58481143, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent2×

Procedure

Ethyl 2-(4-acetyl-3-nitrophenoxy)acetate (TU3205-034) (111 mg) in MeOH (5 mL) was hydrogenated using 10% palladium on charcoal (11 mg) under atomospheric pressure of H2 at ambient temperature. After 30 minutes LC-MS analysis revealed a clean complete reaction. The reaction was repeated using TU3205-034 (1.45 g), 10% palladium on charcoal (140 mg), and MeOH (80 mL). The two reaction mixtures were combined, and the spent catalyst was removed by filtration through a celite pad. The filtrate was concentrated under reduced pressure, affording ethyl 2-(4-acetyl-3-aminophenoxy)acetate (TU3205-036) as a dark yellow oil. MS (ESI+): calcd. 238.10. found 238.10 (MH+). H-NMR (400 MHz, CDCl3): 1.295 (3H, t, J=7.0 Hz), 2.507 (3H, s), 4.269 (2H, q, J=7.2 Hz), 4.603 (2H, s), 6.047 (1H, d, J=2.8 Hz), 6.236 (1H, dd, J=8.8 Hz, 2.8 Hz), 6.396 (2H, br.s), 7.647 (1H, d, J=9.2 Hz). C-NMR (100 MHz, CDCl3): 14.135, 27.658, 61.532, 64.939, 100.237, 104.030, 113.586, 134.286, 152.468, 162.294, 168.310, 199.055.

Workup

  1. customat ambient temperature
  2. customa clean complete reaction
  3. customThe two reaction mixtures
  4. customthe spent catalyst was removed by filtration through a celite pad
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ca340a7bd7db4e86b4c765733d99e956
Source dataset
uspto-grants-2014_07
Patent number
US08785151B2

Reaction notes

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