Phthalimide → HCID 22722273, compound

HRID 1581720Notes

Reaction equation

HRID 1581720 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=[O:3].C[C:8]1[NH:9][C:10]2[C:15]([CH:16]=1)=[CH:14][C:13]([N+:17]([O-:19])=[O:18])=[CH:12][CH:11]=2.C1(=O)[NH:24]C(=O)C2=CC=CC=C12>CCOCC>[NH2:24][C:1](=[O:5])[C:2]([C:16]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([N+:17]([O-:19])=[O:18])[CH:14]=2)[NH:9][CH:8]=1)=[O:3]

Participants

5

Reactant 3

HCID 6809PhthalimideHCID 65578Oxalyl chlorideHCID 2803132-Methyl-5-nitro-1H-indole

Product 1

HCID 22722273HCID 22722273, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
24 °C

Procedure

Oxalyl chloride (4.4 mmol) is added dropwise to a suspension of 2-methyl-5-nitroindole (1.4 mmol) and phthalimide (0.1 g) in ether (10 mL) and the mixture stirred 48 h at 24° C. The reaction vessel is then equipped with a Dewar condenser, chilled to 0° C., and anhydrous ammonia bubbled through the mixture during 1.5 h. The gas and solvent are removed in vacuo. The resulting tan solid is triturated with water, filtered, and the retentate washed with toluene. The solid is dried, affording (2-amino)-1-(5-nitro-1H-indol-3-yl)-ethane-1,2-dione. A portion of this compound (0.59 mmol is taken into THF (15 mL) and treated with borane-THF (2.4 mL of 1 M solution) 16 h at 28° C. The reaction is neutralized with sodium bicarbonate and extracted with ethyl acetate. The ethyl acetate extract is dried in vacuo, redissolved in ethanol (10 mL) and refluxed in the presence of cesium fluoride (360 mg) and sodium carbonate (312 mg). The mixture is filtered through Celite, evaporated and the residue chromatographed on silica gel using chloroform-methanol-ammonia (8:2:0.2) as eluent affording 2-(2-methyl-5-nitro-1H-indol-3-yl)-ethylamine. This compound is acetylated, hydrogenated and transformed to the carbamic acid methyl ester as above.

Workup

  1. customThe reaction vessel is then equipped with a Dewar condenser
  2. temperaturechilled to 0° C.
  3. customanhydrous ammonia bubbled through the mixture during 1.5 h
  4. customThe gas and solvent are removed in vacuo
  5. customThe resulting tan solid is triturated with water
  6. filtrationfiltered
  7. washthe retentate washed with toluene
  8. customThe solid is dried

Sources & evidence

ORD record
ord-6a6381d2c8c24a2da7436e96c428191d
Source dataset
uspto-grants-2004_05
Patent number
US06730707B2

Reaction notes

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