Butanal → HCID 71086476, compound

HRID 528911Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([NH2:14])[CH:9]=2)=[CH:4][CH:3]=1.[CH:15](=O)[CH2:16][CH2:17][CH3:18]>>[CH2:15]([NH:14][C:10]1[CH:9]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[CH:13]=[CH:12][CH:11]=1)[CH2:16][CH2:17][CH3:18]

Participants

Reactant 2

HCID 261Butanal

HCID 27574224'-Chloro-[1,1'-biphenyl]-3-amine

Product 1

HCID 71086476HCID 71086476, compoundYield 82.5%

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 137, 4′-chlorobiphenyl-3-amine (ChemBridge, 285 mg, 1.40 mmol) and butyraldehyde (125 μL, 1.40 mmol) were converted to the title compound (300 mg, 74%). 1H NMR (CDCl3) δ 7.73-7.62 (m, 2H), 7.57-7.44 (m, 3H), 7.43-7.34 (m, 2H), 7.29-7.19 (m, 1H), 3.04-2.96 (m, 2H), 1.67-1.59 (m, 2H), 1.47 (dd, J=15.1, 7.4 Hz, 2H), 0.99 (t, J=7.3 Hz, 3H); MS (ESI+) m/z 260.2 (M+H)+.

Sources & evidence

ORD record: ord-9362afc340444b16b8bb6529a50499dd
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346795B2

Reaction notes

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