Hydrochloric Acid → 4-Cyclobutyl-2-methyl-5-(methylcarbamoyl)benzoic acid

HRID 1487920Notes

Reaction equation

[CH:1]1([C:5]2[C:13]([C:14](OC)=[O:15])=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[C:7]([CH3:18])[CH:6]=2)[CH2:4][CH2:3][CH2:2]1.[CH3:19][NH2:20].Cl>O>[CH:1]1([C:5]2[C:13]([C:14](=[O:15])[NH:20][CH3:19])=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[C:7]([CH3:18])[CH:6]=2)[CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 120 °C

Procedure

Into a 20-mL sealed tube, was placed 4-cyclobutyl-5-(methoxycarbonyl)-2-methylbenzoic acid (compound 62.2, 1.0 g, 4.0 mmol) and methylamine (30% in ethanol) (8 mL). The resulting solution was stirred overnight at 120° C. behind a blast shield, then cooled and diluted with H2O (20 mL). The pH of the solution was adjusted to 4-5 with hydrogen chloride (1 M) and the solids were collected by filtration. The crude product was re-crystallized from ethyl acetate/petroleum ether in the ratio of 1:10 to yield the title compound as an off-white solid (500 mg, 50%).

Workup

customInto a 20-mL sealed tube
temperaturecooled
filtrationthe solids were collected by filtration
customThe crude product was re-crystallized from ethyl acetate/petroleum ether in the ratio of 1:10

Sources & evidence

ORD record: ord-fabf85f05b444dfc9cfe5c546e6fe72b
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428502B2

Reaction notes

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