Hydrochloric Acid → 9-(2-aminoethyl)-1,7,8,9-tetrahydro-indeno[5,4-b][1,4]oxazin-2(3H)-one

HRID 324653Notes

Reaction equation

HRID 324653 reaction equation
[O:1]=[C:2]1[CH2:7][O:6][C:5]2[CH:8]=[CH:9][C:10]3[CH2:11][CH2:12]/[C:13](=[CH:15]\[C:16]#[N:17])/[C:14]=3[C:4]=2[NH:3]1.Cl>[Ni].N.C(O)C>[NH2:17][CH2:16][CH2:15][CH:13]1[C:14]2[C:4]3[NH:3][C:2](=[O:1])[CH2:7][O:6][C:5]=3[CH:8]=[CH:9][C:10]=2[CH2:11][CH2:12]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 11009653(E)-(1,2,3,7,8,9-Hexahydro-2-oxoindeno[5,4-b][1,4] oxazin-9-ylidene)acetonitrile

Product 1

HCID 111281719-(2-aminoethyl)-1,7,8,9-tetrahydro-indeno[5,4-b][1,4]oxazin-2(3H)-oneYield 62%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 22020343Ethanol, reaction products with ammonia, distn. residuesSolvent

Conditions

Temperature
40 °C

Procedure

(E)-(1,2,3,7,8,9-Hexahydro-2-oxoindeno[5,4-b][1,4] oxazin-9-ylidene)acetonitrile (3.0 g, 13.3 mmol.) and Raney nickel (14.0 g) were suspended in a saturated ammonia/ethanol solution (300 mL). The suspension was stirred for 6 hours at 40° C. under hydrogen atmosphere (5 kgf/cm2). The reaction mixture was cooled, and, then, the Raney nickel catalyst was filtered off. From the filtrate, the solvent was distilled off under reduced pressure to leave an oily residue. The residue was poured into 2N HCl, which was washed with ethyl acetate. The pH of the aqueous layer was adjusted to 10 with a 4N aqueous solution of sodium hydroxide. The organic matter was extracted from the aqueous layer with a mixture solvent of chloroform/methanol (10:1). The extract solution was dried over anhydrous magnesium sulfate, then the solvent was distilled off under reduced pressure. The residue was recrystallized from ethyl acetate/isopropyl ether to afford the title compound (yield 1.9 g, 62%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationthe Raney nickel catalyst was filtered off
  3. distillationFrom the filtrate, the solvent was distilled off under reduced pressure
  4. customto leave an oily residue
  5. washwas washed with ethyl acetate
  6. extractionThe organic matter was extracted from the aqueous layer with a mixture solvent of chloroform/methanol (10:1)
  7. dry with materialThe extract solution was dried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was recrystallized from ethyl acetate/isopropyl ether

Sources & evidence

ORD record
ord-2759938794b74d8b9a6278b96577cdbb
Source dataset
uspto-grants-2001_04
Patent number
US06218429B1

Reaction notes

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