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

HRID 604269
Notes
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Reaction equation

HRID 604269 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 598492094-(4-Isopropyl-piperazin-1-yl)-2-methyl-7-nitro-2,3-dihydro-isoindol-1-one

Product 1

HCID 598492047-amino-2-methyl-4-(4-propan-2-ylpiperazin-1-yl)-3H-isoindol-1-oneYield 85%

Reagents, catalysts & solvents 2

HCID 23925IronCatalyst
HCID 702
Ethanol
Solvent

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

  1. additionis added
  2. temperatureThe mixture is cooled
  3. customAfter removing insoluble materials
  4. filtrationby filtration
  5. customthe mixture is evaporated
  6. filtrationThe resulting pale yellow solids are collected by filtration
  7. 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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