Butanal → HCID 23465406, compound

HRID 528901Notes

Reaction equation

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

Participants

Reactant 2

HCID 261Butanal

HCID 72553-Chloro-4-methylaniline

Product 1

HCID 23465406HCID 23465406, compoundYield 97%

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 137, 3-chloro-p-toluidine (Aldrich, 430 μL, 3.53 mmol) and butyraldehyde (320 μL, 3.13 mmol) were converted to the title compound (600 mg, 79%). 1H NMR (CDCl3) δ 7.06-6.93 (m, 1H), 6.62 (d, J=2.4 Hz, 1H), 6.43 (dd, J=8.1, 2.4 Hz, 1H), 3.56 (br s, 1H), 3.08 (t, J=7.2 Hz, 2H), 2.26 (s, 3H), 1.66-1.50 (m, 2H), 1.49-1.33 (m, 2H), 1.00-0.89 (m, 3H).

Sources & evidence

ORD record: ord-373ac92fef3c4345945f3d00c285aea8
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346795B2

Reaction notes

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