3-amino-N-cyclopropyl-4-methylbenzamide → 3-(7-bromo-1,3-dioxo-3,4-dihydroisoquinolin-2(1H)-yl)-N-cyclopropyl-4-methylbenzamide

HRID 506968Notes

Reaction equation

[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][C:7](=[O:13])O[C:9]2=[O:12])=[CH:4][CH:3]=1.[NH2:14][C:15]1[CH:16]=[C:17]([CH:24]=[CH:25][C:26]=1[CH3:27])[C:18]([NH:20][CH:21]1[CH2:23][CH2:22]1)=[O:19]>C1(C)C=CC=CC=1.C(O)(=O)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][C:7](=[O:13])[N:14]([C:15]3[CH:16]=[C:17]([CH:24]=[CH:25][C:26]=3[CH3:27])[C:18]([NH:20][CH:21]3[CH2:22][CH2:23]3)=[O:19])[C:9]2=[O:12])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A suspension of 7-bromo-1H-isochromene-1,3(4H)-dione (1.09 g) and 3-amino-N-cyclopropyl-4-methylbenzamide (0.91 g) in a mixture of toluene (8 ml) and acetic acid (2.5 ml) was heated under microwave irradiation conditions (Personal Chemistry Emrys Optimizer with 300 W magnetron) at 150° C. for 60 minutes. This was process was repeated and the batches combined, diluted with ethyl acetate and washed with 1N HCl, saturated NaHCO3 solution, water, brine, dried (magnesium sulfate) to yield 3-(7-bromo-1,3-dioxo-3,4-dihydroisoquinolin-2(1H)-yl)-N-cyclopropyl-4-methylbenzamide as a brown solid (1.13 g); NMR Spectrum: (DMSOd6) 0.60 (m, 2H), 0.71 (m, 2H), 2.12 (s, 3H), 2.89 (m, 1H), 4.34 (d, 1H), 4.42 (d, 1H), 7.48 (d, 1H), 7.53 (d, 1H), 7.70 (s, 1H), 7.85 (d, 1H), 7.99 (d, 1H), 8.20 (s, 1H), 8.45 (d, 1H); Mass Spectrum: M+Na+ 435.

Workup

washwashed with 1N HCl, saturated NaHCO3 solution, water, brine
dry with materialdried (magnesium sulfate)

Sources & evidence

ORD record: ord-357ca41083ef49cab05648ef19b6c405
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07786115B2

Reaction notes

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