Butanal → Benzoic acid, 4-(butylamino)-, methyl ester

HRID 528912Notes

Reaction equation

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

Participants

Reactant 2

HCID 261Butanal

HCID 12082Methyl 4-aminobenzoate

Product 1

HCID 12045722Benzoic acid, 4-(butylamino)-, methyl esterYield 87.5%

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 137, 4-aminobenzoic acid methyl ester (Aldrich, 500 mg, 3.31 mmol) and butyraldehyde (300 μL, 3.31 mmol) were converted to the title compound (600 mg, 82%). 1H NMR (CDCl3) δ 7.91-7.80 (m, 2H), 6.59-6.46 (m, 2H), 3.86 (s, 3H), 3.18 (t, J=7.0 Hz, 2H), 1.67-1.58 (m, 2H), 1.48-1.37 (m, 2H), 0.98 (t, J=7.4 Hz, 3H); MS(ESI+) m/z 208.1 (M+H)+.

Sources & evidence

ORD record: ord-f38c327615ab4310b66ca39b198bb472
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346795B2

Reaction notes

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