Butanal → HCID 28969529, compound

HRID 528900Notes

Reaction equation

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

Participants

Reactant 2

HCID 261Butanal

HCID 821124-Isopropoxyaniline

Product 1

HCID 28969529HCID 28969529, compoundYield 87.4%

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 137, 4-isopropoxyaniline (500 mg, 3.31 mmol) and butyraldehyde (300 μL, 3.31 mmol) were converted to the title compound (600 mg, 83%). 1H NMR (CDCl3) δ 6.88-6.74 (m, 2H), 6.67-6.51 (m, 2H), 4.41-4.30 (m, 1H), 3.08 (t, J=7.0 Hz, 2H), 1.66-1.37 (m, 4H), 1.30 (s, 3H), 1.29 (s, 3H), 0.99-0.87 (m, 3H); MS(ESI+) m/z 208.2 (M+H)+.

Sources & evidence

ORD record: ord-6cc53adbaf7247de833ae85ed9ceb40d
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346795B2

Reaction notes

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