4-Methyl-2-nitro-1-(1-propen-2-yl)benzene → 2-Isopropyl-5-methylaniline

HRID 62040

Reaction equation

HRID 62040 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:10])=[CH2:9])=[C:4]([N+:11]([O-])=O)[CH:3]=1>[Pd].C(OCC)(=O)C>[CH:8]([C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][C:4]=1[NH2:11])([CH3:10])[CH3:9]

Participants

4

Reactant 1

HCID 897388014-Methyl-2-nitro-1-(1-propen-2-yl)benzene

Product 1

HCID 205638272-Isopropyl-5-methylaniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To 4-methyl-2-nitro-1-(prop-1-en-2-yl)benzene (0.986 g, 5.56 mmol) in a 100 mL round-bottomed flask equipped with a stir bar was added ethyl acetate (55.6 mL) and palladium on carbon (1.18 g, 0.556 mmol). The reaction was evacuated and backfilled with hydrogen (balloon). The reaction was stirred under an atmosphere of hydrogen overnight. The reaction mixture was filtered through a pad of Celite® and concentrated providing the title compound as a clear and colorless oil (0.788 g, 95%): IR (thin film) 3464 (m), 3372 (m), 3011 (m), 2959 (s), 2869 (m), 1621 (m), 1575 (m), 1509 (m) cm−1; 1H NMR (400 MHz, CDCl3) δ 7.03 (d, J=7.8 Hz, 1H), 6.61 (dd, J=7.8, 1.7 Hz, 1H), 6.54-6.50 (m, 1H), 3.59 (bs, 2H), 2.87 (hept, J=6.8 Hz, 1H), 2.24 (s, 3H), 1.24 (d, J=6.8 Hz, 6H); 13C NMR (101 MHz, CDCl3) δ 143.14, 136.16, 129.82, 125.33, 119.79, 116.55, 99.97, 27.36, 22.41, 20.96.

Workup

  1. customThe reaction was evacuated
  2. filtrationThe reaction mixture was filtered through a pad of Celite®
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-a7b10ddd258843ada25dc2104feb89ae
Source dataset
uspto-grants-2016_09
Patent number
US09445594B2

Linked notes

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