HCID 22326827, compound → HCID 22326890, compound

HRID 491620Notes

Reaction equation

HRID 491620 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-])=O)=[CH:5][C:4]=1[CH2:12][CH2:13][N:14]([CH3:16])[CH3:15]>CCO.[Pd]>[CH3:16][N:14]([CH3:15])[CH2:13][CH2:12][C:4]1[CH:5]=[C:6]([NH2:9])[CH:7]=[CH:8][C:3]=1[O:2][CH3:1]

Participants

4

Reactant 1

HCID 22326827HCID 22326827, compound

Product 1

HCID 22326890HCID 22326890, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of [2-(2-methoxy-5-nitrophenyl)-ethyl]-dimethyl-amine (1.0 g, Step D) dissolved in EtOH (20 mL) was added 10% Pd/C (0.1 g). The reaction vessel was capped with a rubber septum and H2 gas was introduced through a balloon/needle. The reaction was stirred vigorously overnight at RT, and which time it was filtered through sand/Celite®. Concentration of the crude mixture provided a beige oil which was purified by chromatography on silica gel (97:3 CH2Cl2:MeOH) to afford pure 3-(2-dimethylamino-ethyl)-4-methoxy-phenylamine as a white solid.

Workup

  1. customThe reaction vessel was capped with a rubber septum and H2 gas
  2. additionwas introduced through a balloon/needle
  3. filtrationwhich time it was filtered through sand/Celite®
  4. customConcentration of the crude mixture provided a beige oil which
  5. customwas purified by chromatography on silica gel (97:3 CH2Cl2:MeOH)

Sources & evidence

ORD record
ord-c4eaec3cf6fb4d19b26c8b4e5d0cca25
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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