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

HRID 62040

反応式

HRID 62040 の反応式
[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]

参加物

4

反応物 1

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

生成物 1

HCID 205638272-Isopropyl-5-methylaniline

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-a7b10ddd258843ada25dc2104feb89ae
出典データセット
uspto-grants-2016_09
特許番号
US09445594B2

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