1-(2,2-Dimethoxyethyl)-3-methyl-2-nitrobenzene → 2-(2,2-Dimethoxyethyl)-6-methylaniline

HRID 751482Notes

Reaction equation

HRID 751482 reaction equation
[CH3:1][O:2][CH:3]([O:15][CH3:16])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:6]=1[N+:12]([O-])=O>CO.[Pd]>[CH3:1][O:2][CH:3]([O:15][CH3:16])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:6]=1[NH2:12]

Participants

4

Reactant 1

HCID 692699561-(2,2-Dimethoxyethyl)-3-methyl-2-nitrobenzene

Product 1

HCID 128753252-(2,2-Dimethoxyethyl)-6-methylanilineYield 103%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Add to a round bottomed flask containing 1-(2,2-dimethoxyethyl)-3-methyl-2-nitrobenzene (1.1 g) in methanol (50 mL), 10% palladium on carbon (0.13 g). Purge with nitrogen then place under a hydrogen atmosphere using a balloon of hydrogen. Stir overnight at room temperature. Filter through Celite, wash with methanol. Concentrate to give product (0.98 g, 103%) as a clear oil. 1H NMR (400 MHz, DMSO-d6) δ 2.05 (s, 3H), 2.71 (d, J=5.36 Hz, 211), 3.23 (s, 6H), 4.52 (m, 3H), 6.42 (m, 1H), 6.80 (d, J=7.31 Hz, 2H).

Workup

  1. additionAdd to a round bottomed flask
  2. customPurge with nitrogen
  3. filtrationFilter through Celite
  4. washwash with methanol
  5. concentrationConcentrate

Sources & evidence

ORD record
ord-6c544070826e445da30ad60e90087876
Source dataset
uspto-grants-2008_07
Patent number
US07405305B2

Reaction notes

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