Butanal → N-Butyl-3,4-dichloroaniline

HRID 528893Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[Cl:9])[NH2:5].[CH:10](=O)[CH2:11][CH2:12][CH3:13]>>[CH2:10]([NH:5][C:4]1[CH:6]=[CH:7][C:8]([Cl:9])=[C:2]([Cl:1])[CH:3]=1)[CH2:11][CH2:12][CH3:13]

Participants

Reactant 2

HCID 261Butanal

HCID 72573,4-Dichloroaniline

Product 1

HCID 29276966N-Butyl-3,4-dichloroanilineYield 57%

Procedure

Following a procedure analogous to that for the synthesis of Example 106, 3,4-dichloroaniline (1.62 g, 10.0 mmol) and butyraldehyde (721 mg, 10.0 mmol) were converted to the title compound (1.24 g, 57%). 1H NMR (CDCl3) δ 7.17 (d, J=8.8 Hz, 1H), 6.65 (d, J=2.9 Hz, 1H), 6.41 (dd, J=2.8, 8.7 Hz, 1H), 3.05 (t, J=7.0 Hz, 2H), 1.65-1.53 (m, 2H), 1.43 (qd, J=7.3, 15.0 Hz, 2H), 0.98 (t, J=7.4 Hz, 3H); MS(ESI+) m/z 218.1 (M+H)+.

Sources & evidence

ORD record: ord-8aa454323849426c80810f0143072a29
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346795B2

Reaction notes

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