Butanal → HCID 71086469, compound

HRID 528904Notes

Reaction equation

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

Participants

Reactant 2

HCID 261Butanal

HCID 793343-tert-Butylaniline

Product 1

HCID 71086469HCID 71086469, compoundYield 87.2%

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 137, 3-tert-butylaniline (500 mg, 3.35 mmol) and butyraldehyde (300 μL, 3.35 mmol) were converted to the title compound (600 mg, 80%). 1H NMR (CDCl3) δ 7.15 (t, J=7.8 Hz, 1H), 6.79-6.74 (m, 1H), 6.66 (t, J=2.1 Hz, 1H), 6.47 (ddd, J=8.0, 2.3, 0.7 Hz, 1H), 3.61 (br s, 1H), 3.14 (t, J=7.0 Hz, 2H), 1.69-1.55 (m, 2H), 1.53-1.42 (m, 2H), 1.32 (s, 9H), 0.99 (t, J=7.3 Hz, 3H).

Sources & evidence

ORD record: ord-6da1ec7d5d5847628d02d0af48e01985
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346795B2

Reaction notes

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