2-Methyl-4-propoxyaniline → 4-Butoxy-2-methylaniline

HRID 2174515Notes

Reaction equation

HRID 2174515 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[C:8]([CH3:15])[CH:7]=1)[CH2:2][CH2:3][CH3:4].CC1C=C(OCCC)C=CC=1N>>[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[C:8]([CH3:15])[CH:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 167893412-Methyl-4-propoxyanilineHCID 692098674-Butoxy-2-methyl-1-nitrobenzene

Product 1

HCID 167852134-Butoxy-2-methylanilineYield 90%

Procedure

This compound was prepared from 404d (1.92 g, 9.2 mmol) in a manner similar to that for 405b yielding an amber oil (1.48 g, 90%): TLC Rf 0.28 (20% EtOAc/hexanes). 1NMR (600 MHz, CDCl3) δ 6.67 (s, 1H), 6.62 (m, 2H), 3.89-3.87 (t, 2H, J=6.54 Hz), 2.16 (s, 3H), 1.73-1.70 (quin, 2H, J=6.6 Hz), 1.49-1.45 (sex, 2H, J=7.5 Hz), 0.97-0.95 (t, 3H, J=7.38 Hz). 13C NMR (150 MHz, CDCl3) δ 152.4, 137.8, 124.2, 117.24, 116.13, 112.9, 68.3, 31.5, 19.3, 17.7, 13.9. Elemental analysis calculated for C11H17NO: C, 73.70; H, 9.56; N, 7.81. Found: C, 73.55; H, 9.51; N, 7.96.

Sources & evidence

ORD record
ord-2bfa000d97734ab7925ea49e91f2bc91
Source dataset
uspto-grants-2015_06
Patent number
US09061994B1

Reaction notes

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