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

HRID 62040

반응식

HRID 62040 반응식
[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]

참가 물질

4

반응물 1

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

생성물 1

HCID 205638272-Isopropyl-5-methylaniline

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-a7b10ddd258843ada25dc2104feb89ae
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09445594B2

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