Hydrochloric Acid → 7-amino-2-methyl-4-(4-propan-2-ylpiperazin-1-yl)-3H-isoindol-1-one

HRID 604269Notes

Reaction equation

[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[C:15]3[C:11]=2[CH2:12][N:13]([CH3:23])[C:14]3=[O:22])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].Cl.[OH-].[Na+]>C(O)C.[Fe]>[NH2:19][C:16]1[CH:17]=[CH:18][C:10]([N:7]2[CH2:6][CH2:5][N:4]([CH:1]([CH3:3])[CH3:2])[CH2:9][CH2:8]2)=[C:11]2[C:15]=1[C:14](=[O:22])[N:13]([CH3:23])[CH2:12]2

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 4-(4-Isopropyl-piperazin-1-yl)-2-methyl-7-nitro-2,3-dihydro-isoindol-1-one (4.56 g, 14 mmol) in ethanol (130 mL), iron powder (4.0 g, 70 mmol) and 1N hydrochloric acid (28 mL) are the mixture is added stirred at 60° C. for 3 hours. The mixture is cooled and then, 1N sodium hydroxide (28 mL) is added. After removing insoluble materials by filtration, the mixture is evaporated. The resulting pale yellow solids are collected by filtration and dried in vacuo at 50° C. to afford 7-Amino-4-(4-isopropyl-piperazin-1-yl)-2-methyl-2,3-dihydro-isoindol-1-one (3.43 g) as brown solids in 83% yield. Rf=0.18 (Hexane/AcOEt=111). 1H-NMR (400 MHz, CDCl3, δ, ppm): 1.09 (s, 3H), 1.10 (s, 3H), 2.65 (t, 4H), 2.75-2.69 (m, 1H), 2.96 (t, 4H), 3.13 (s, 3H), 4.28 (s, 2H), 4.99 (s, 2H), 6.56 (d, 1H), 6.99 (d, 1H).

Workup

additionis added
temperatureThe mixture is cooled
customAfter removing insoluble materials
filtrationby filtration
customthe mixture is evaporated
filtrationThe resulting pale yellow solids are collected by filtration
customdried in vacuo at 50° C.

Sources & evidence

ORD record: ord-b19f3fb547594091a80bcd849c829360
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07910585B2

Reaction notes

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