1-(2-Chloroethoxy)-2-methyl-3-nitrobenzene → HCID 53669114, compound

HRID 363005Notes

Reaction equation

HRID 363005 reaction equation
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-])=O)[C:6]=1[CH3:14]>C(O)C.[Pd]>[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH2:11])[C:6]=1[CH3:14]

Participants

4

Reactant 1

HCID 434379591-(2-Chloroethoxy)-2-methyl-3-nitrobenzene

Product 1

HCID 53669114HCID 53669114, compoundYield 98.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1-(2-chloroethoxy)-2-methyl-3-nitrobenzene (10.7 g, 50 mmol) in ethanol (200 mL) containing 500 mg of 5% palladium on carbon was hydrogenated at 50 psi for 4 h. The catalyst was filter through Solka Floc and the solvent removed under vacuum to afford 9.1 g (98.8%) a yellow oil: 1H NMR (CDCl3) δ 2.76 (3H, s), 3.92 (2H, t, J=5.9 Hz), 4.40 (2H, t, J=5.9 Hz), 6.70 (1H, d, J=), 7.46 (1H, app t, J=), 8.04 (1H, d, J=), 8.24 (1H, s).

Workup

  1. filtrationThe catalyst was filter through Solka Floc
  2. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-28d6ecfa755a4748b5a77698481bab09
Source dataset
uspto-grants-1999_02
Patent number
US05872144

Reaction notes

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