Butanal → N-butyl-4-methoxyaniline

HRID 528902Notes

Reaction equation

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

Participants

Reactant 2

HCID 261Butanal

HCID 7732P-Anisidine

Product 1

HCID 11389741N-butyl-4-methoxyanilineYield 96.2%

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 137, 4-methoxyaniline (500 mg, 4.06 mmol) and butyraldehyde (360 μL, 4.06 mmol) were converted to the title compound (700 mg, 88%). 1H NMR (CDCl3) δ 6.89-6.73 (m, 2H), 6.69-6.50 (m, 2H), 3.76 (s, 3H), 3.10 (t, J=7.2 Hz, 2H), 1.70-1.28 (m, 4H), 1.02-0.90 (m, 3H); MS(ESI+) m/z 180.1 (M+H)+.

Sources & evidence

ORD record: ord-1c91ccc07e004924abd167c0d911b4e2
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346795B2

Reaction notes

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