2-Chloro-1-(2-methoxyethoxy)-4-nitrobenzene → 3-Chloro-4-(2-methoxyethoxy)aniline

HRID 1159929Notes

Reaction equation

HRID 1159929 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[O:11][CH2:12][CH2:13][O:14][CH3:15]>CCOC(C)=O.C(O)C.[Pt]>[Cl:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]=1[O:11][CH2:12][CH2:13][O:14][CH3:15])[NH2:8]

Participants

5

Reactant 1

HCID 595137122-Chloro-1-(2-methoxyethoxy)-4-nitrobenzene

Product 1

HCID 64857493-Chloro-4-(2-methoxyethoxy)anilineYield 97.6%

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Chloro-1-{[2-(methyloxy)ethyl]oxy}-4-nitrobenzene (1.0 g) was dissolved in a 1:1 solution of EtOAc and ethanol (30 mL). Pt/C (0.15 g of 10% by weight) was added and the resulting mixture was placed under 50 psi of H2 for 16 h. The reaction was then filtered through celite and the resulting organics were concentrated in vacuo to obtain 0.85 g of the compound. 1H NMR (300 MHz, DMSO-d6): δ 6.88 (d, 1H), 6.66 (m, 1H), 6.50 (m, 1H), 4.00 (m, 2H), 3.63 (m, 2H), 3.33 (s, 3H).

Workup

  1. filtrationThe reaction was then filtered through celite
  2. concentrationthe resulting organics were concentrated in vacuo

Sources & evidence

ORD record
ord-35b927438199451f9f1267fdd9271980
Source dataset
uspto-grants-2010_10
Patent number
US07812022B2

Reaction notes

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