Acetone → HCID 66884305, compound

HRID 915357Notes

Reaction equation

[C:1]([CH2:4][C:5]1[C:13]([Cl:14])=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=O)([OH:3])=O.[CH3:15][C:16]1[CH:23]=[C:22]([CH3:24])[CH:21]=[CH:20][C:17]=1[CH2:18][NH2:19].CC(C)=O.CO>C(Cl)Cl>[Cl:14][C:13]1[CH:12]=[CH:11][CH:10]=[C:6]2[C:5]=1[CH2:4][C:1](=[O:3])[N:19]([CH2:18][C:17]1[CH:20]=[CH:21][C:22]([CH3:24])=[CH:23][C:16]=1[CH3:15])[C:7]2=[O:9]

Participants

Conditions

Temperature: 180 °C

Procedure

A mixture of 2-carboxymethyl-3-chlorobenzoic acid (1.91 g, 8.9 mmol) and 2,4-dimethylbenzylamine (1.35 mL, 9.6 mmol) was placed in a vented vial and heated in an oil bath maintained at 180° C. After heating for 64 hours the reaction was allowed to cool to ambient temperature, then taken up in a mixture of CH2Cl2, acetone, and methanol. The solution was mixed with silica gel and then concentrated under reduced pressure to afford a free flowing solid. This solid was loaded onto the top of a silica gel column and eluted with a gradient from 0% to 14% ethyl acetate/hexane to afford 5-chloro-2-(2,4-dimethylbenzyl)-4H-isoquinoline-1,3-dione (2.03 g, 73% yield) as a yellow solid: 1H-NMR (400 MHz, CDCl3): δ 8.17 (1H, dd, J=7.8, 1.3 Hz), 7.65 (1H, dd, J=7.8, 1.3 Hz), 7.42 (1H, app. t, J=7.8 Hz), 6.98 (1H, br s), 6.96-6.92 (1H, m), 6.91-6.87 (1H, m), 5.16 (2H, s), 4.09 (2H, s), 2.44 (3H, s), 2.26 (3H, s) ppm.

Workup

temperatureheated in an oil bath
temperatureAfter heating for 64 hours the reaction
temperatureto cool to ambient temperature
additionThe solution was mixed with silica gel
concentrationconcentrated under reduced pressure
customto afford
washeluted with a gradient from 0% to 14% ethyl acetate/hexane

Sources & evidence

ORD record: ord-70f09bf14a584303ba0819446e767188
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07265131B2

Reaction notes

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