Butanal → HCID 58942896, compound

HRID 528913Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.[CH:14](=O)[CH2:15][CH2:16][CH3:17]>>[CH2:14]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:6][CH:7]=1)[CH2:15][CH2:16][CH3:17]

Participants

Reactant 2

HCID 261Butanal

HCID 225219p-Aminophenylacetic acid ethyl ester

Product 1

HCID 58942896HCID 58942896, compoundYield 91.4%

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 137, ethyl 2-(4-aminophenyl)acetate (500 mg, 2.79 mmol) and butyraldehyde (250 μL, 2.79 mmol) were converted to the title compound (600 mg, 87%). 1H NMR (CDCl3) δ 7.12-7.04 (m, 2H), 6.60-6.52 (m, 2H), 4.14 (q, J=7.0 Hz, 2H), 3.49 (s, 2H), 3.11 (t, J=7.0 Hz, 2H), 1.66-1.50 (m, 2H), 1.50-1.36 (m, 2H), 1.25 (t, J=7.0 Hz, 3H), 0.96 (t, J=7.3 Hz, 3H); MS(ESI+) m/z 236.3 (M+H)+.

Sources & evidence

ORD record: ord-1ea786fe59b14226862a9618dcf509fe
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346795B2

Reaction notes

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