N-Aminophthalimide → 2-[2-(2-chloro-4-methoxyphenyl)-3-methyl-1H-pyrrol-1-yl]-1H-isoindole-1,3(2H)-dione

HRID 1827742Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10](=O)[CH:11]([CH3:15])[CH2:12][CH:13]=O.[NH2:17][N:18]1[C:22](=[O:23])[C:21]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]2[C:19]1=[O:28]>Cl.O1CCOCC1>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]1[N:17]([N:18]2[C:22](=[O:23])[C:21]3[C:20](=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:19]2=[O:28])[CH:13]=[CH:12][C:11]=1[CH3:15]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-(2-chloro-4-methoxyphenyl)-3-methyl-4-oxobutanal (6.40 g, 27.0 mmol) and N-aminophthalimide (5.32 g, 29.0 mmol) in HCl (5N, 3.90 mL) and dioxane (100 mL) was heated at 100° C. for 1 h. After cooling down to room temperature, the mixture was concentrated in vacuo and the residue was recrystalized from CH2Cl2/hepatene to give 9.22 g (95%) of pink solid as the title compound: mp 202.0–208.5° C.; 1H NMR (400 MHz, Acetone-d6) δ 7.95–7.86 (m, 4H), 7.17 (d, J=8.6 Hz, 1H), 7.01 (d, J=3.1 Hz, 1H), 6.99 (d, J=2.6 Hz, 1H), 6.82 (dd, J=8.6, 2.6 Hz, 1H), 6.20 (d, J=3.1 Hz, 1H), 3.77 (s, 3H), 1.98 (s, 3H); IR (diffuse reflectance) 2072, 2014, 1981, 1906, 1747, 1463, 1293, 1275, 1214, 1047, 881, 820, 719, 712, 705 cm−1; HRMS (FAB) calcd for C20H15N2O3Cl+H 367.0849. found 367.0832. Anal. Calcd for C20H15N2O3Cl: C, 65.49; H, 4.12; N, 7.64. Found: C, 65.16; H, 3.99; N, 7.58.

Workup

temperatureAfter cooling down to room temperature
concentrationthe mixture was concentrated in vacuo
customthe residue was recrystalized from CH2Cl2/hepatene

Sources & evidence

ORD record: ord-7b7e75efd1f8417a8d9f31696f7d5f88
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07056920B2

Reaction notes

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