1-Iodopropane → HCID 21298232, compound

HRID 34659Notes

Reaction equation

HRID 34659 reaction equation
[O:1]1[C:5]2[C:6]3[CH:7]=[CH:8][CH:9]=[N:10][C:11]=3[CH2:12][CH2:13][C:4]=2[N:3]=[C:2]1[NH2:14].I[CH2:16][CH2:17][CH3:18]>C(#N)C>[CH2:16]([N:10]1[CH:11]2[C:6]([C:5]3[O:1][C:2]([NH2:14])=[N:3][C:4]=3[CH2:13][CH2:12]2)=[CH:7][CH2:8][CH2:9]1)[CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 336431-IodopropaneHCID 212982064,5-Dihydrooxazolo[5,4-f]quinolin-2-amine

Product 1

HCID 21298232HCID 21298232, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4,5-dihydrooxazolo[5,4-f]quinolin-2-amine, 5.0 g (26.7 mmol), (Example 27), in 200 ml of acetonitrile is refluxed with 1-iodopropane, 10.2 g (60 mmol), for 24 hours. The volatiles are then removed in-vacuo and the resulting solid is washed with diethyl ether and dried. The resulting 2-amino-4,5-dihydrooxazolo[5,4-f]quinolinium iodide is dissolved in 150 ml of water and treated with sodium borohydride, 1.7 g (50 mmol), in small portions. The mixture is stirred at room temperature for 2 hours. Following acidification with 10% hydrochloric acid, the mixture is stirred for another hour. The volatile components are removed in-vacuo and the residue is partitioned between chloroform and 1% ammonium hydroxide. The organic extract is concentrated and purified by column chromatography to give (±) 4,5,5a,6,7,8-hexahydro-6-propyloxazolo [5,4-f]quinolin-2-amine.

Workup

  1. customThe volatiles are then removed in-vacuo
  2. washthe resulting solid is washed with diethyl ether
  3. customdried
  4. dissolutionThe resulting 2-amino-4,5-dihydrooxazolo[5,4-f]quinolinium iodide is dissolved in 150 ml of water
  5. additiontreated with sodium borohydride, 1.7 g (50 mmol), in small portions
  6. stirringthe mixture is stirred for another hour
  7. customThe volatile components are removed in-vacuo
  8. customthe residue is partitioned between chloroform and 1% ammonium hydroxide
  9. extractionThe organic extract
  10. concentrationis concentrated
  11. custompurified by column chromatography

Sources & evidence

ORD record
ord-bc7426cd493e4512b0f362e05727d081
Source dataset
uspto-grants-1988_08
Patent number
US04762843

Reaction notes

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