1H-Isoindole-1,3(2H)-dione, 2-methyl-4-nitro- → HCID 21138365, compound

HRID 1872702Notes

Reaction equation

HRID 1872702 reaction equation
[N+:1]([C:4]1[CH:15]=[CH:14][CH:13]=[C:6]2[C:7]([N:9]([CH3:12])[C:10](=O)[C:5]=12)=O)([O-])=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[NH2:1][C:4]1[CH:15]=[CH:14][CH:13]=[C:6]2[C:5]=1[CH2:10][N:9]([CH3:12])[CH2:7]2

Participants

4

Reactant 2

HCID 757721H-Isoindole-1,3(2H)-dione, 2-methyl-4-nitro-HCID 21226445Aluminium lithium hydride

Product 1

HCID 21138365HCID 21138365, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-nitro-N-methylphthalimide (0.58 g, 2.8 mmol) in dry tetrahydrofuran (10 ml) was added dropwise to a stirred suspension of lithium aluminium hydride (0.64 g, 16.8 mmol) under argon. The mixture was stirred at room temperature for 2h and then heated under gentle reflux for 2.5h. The reaction was quenched by addition of wet diethyl ether followed by a minimum amount of water. The precipithated aluminium salts were removed by filtration. The filtrate was concentrated in vacuo to give the title compound as a brown oil (400 mg) which was used directly in the next stage (Example 31).

Workup

  1. temperatureheated
  2. temperatureunder gentle reflux for 2.5h
  3. customThe reaction was quenched by addition of wet diethyl ether
  4. customThe precipithated aluminium salts were removed by filtration
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-6e4ef1ba83444814b592d7863c2c432d
Source dataset
uspto-grants-2000_08
Patent number
US06110934

Reaction notes

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