HCID 18702060, compound → HCID 18702062, compound

HRID 2288927Notes

Reaction equation

HRID 2288927 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][CH:18]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=1>[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][CH:18]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=1

Participants

3

Reactant 1

HCID 18702060HCID 18702060, compound

Product 1

HCID 18702062HCID 18702062, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

4-(3-Methoxybenzyl)nitrobenzene (0.50 g, 2.10 mmol) was dissolved in ETOH (25 mL) and 10% palladium on carbon (0.50 g) was added under a nitrogen stream. The reaction mixture was hydrogenated on a Parr shaker at 50 psi for 16 h. The reaction mixture was filtered and the filtrate was concentrated to give 0.34 g (77%) of 4-(3-methoxybenzyl)aniline as an oil. 1H NMR (CDCl3) δ7.15 (t, J=8.1 Hz, 1H), 6.95 (d, J=8.1 Hz, 2H), 6.70 (m, 3H), 6.60 (d, J=8.1 Hz, 2H), 3.85 (s, 2H), 3.75 (s, 3H), 3.45 (bs, 2H).

Workup

  1. additionwas added under a nitrogen stream
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-4c61d6acc28e4bb5bff35e2c3e3f62e2
Source dataset
uspto-grants-2000_07
Patent number
US06090854

Reaction notes

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