Butanal → HCID 28447315, compound

HRID 528899Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[NH2:6].[CH:12](=O)[CH2:13][CH2:14][CH3:15]>>[CH2:12]([NH:6][C:5]1[CH:7]=[CH:8][C:9]([O:10][CH3:11])=[C:3]([O:2][CH3:1])[CH:4]=1)[CH2:13][CH2:14][CH3:15]

Participants

Reactant 2

HCID 261Butanal

HCID 227703,4-Dimethoxyaniline

Product 1

HCID 28447315HCID 28447315, compoundYield 87.9%

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 137, 3,4-dimethoxyaniline (500 mg, 3.26 mmol) and butyraldehyde (290 μL, 3.26 mmol) were converted to the title compound (600 mg, 83%). 1H NMR (CDCl3) δ 6.81-6.70 (m, 1H), 6.27-6.21 (m, 1H), 6.16 (dd, J=8.5, 2.5 Hz, 1H), 3.85 (s, 3H), 3.81 (s, 3H), 3.08 (t, J=7.0 Hz, 2H), 1.56-1.40 (m, 4H), 0.99-0.93 (m, 3H); MS(ESI+) m/z 210.2 (M+H)+.

Sources & evidence

ORD record: ord-d0a8620fb992492cbd8f1ab6d7f41bcd
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346795B2

Reaction notes

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