Potassium Hydroxide → HCID 21423155, compound

HRID 259117Notes

Reaction equation

HRID 259117 reaction equation
[Cl-:1].[Al+3].[Cl-].[Cl-].[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:11]([CH2:13][CH2:14][CH:15]1[CH2:24][C:23]2[CH:22]([O:25][CH3:26])[N:21]([O:27][CH3:28])[CH:20]=[C:19]3[O:29][CH2:30][CH2:31][CH:17]([C:18]=23)[CH2:16]1)#[N:12].[OH-].[K+]>CCOCC.O1CCCC1.O>[ClH:1].[ClH:1].[NH2:12][CH2:11][CH2:13][CH2:14][CH:15]1[CH2:24][C:23]2[CH:22]([O:25][CH3:26])[N:21]([O:27][CH3:28])[CH:20]=[C:19]3[O:29][CH2:30][CH2:31][CH:17]([C:18]=23)[CH2:16]1

Participants

8

Reactant 4

HCID 14797Potassium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 70631280HCID 70631280, compound

Product 1

HCID 21423155HCID 21423155, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent3×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of aluminum chloride (5.6 g) in anhydrous ether (80 ml) is added dropwise to a stirred suspension of lithium aluminum hydride (1.6 g) in anhydrous ether (80 ml). The mixture is stirred at room temperature for 0.5 hr. and then a solution of the nitrile, 5-cyanoethyl-1,2,3a,4,5,6-hexahydro-7,8-dimethoxypyrano[2,3,4-de]isoquinoline (7 g), described in Example 61, in anhydrous ether (100 ml) is added dropwise during 2 hr. The mixture is heated under reflux for 2 hr. and then cooled (ice bath) and a solution of water (12 ml) in tetrahydrofuran (60 ml) is added. The mixture is heated under reflux for 15 minutes, cooled and water (20 ml) is added, followed by 10% KOH solution until the aqueous phase is rendered basic. The mixture is filtered, washing well with ether. The ether solution is collected and the aqueous phase is saturated with salt and extracted with chloroform. The organic solutions are combined and evaporated to yield the title compound, λmaxEtOH 284 nm (1830).

Workup

  1. additionis added dropwise during 2 hr
  2. temperatureThe mixture is heated
  3. temperatureunder reflux for 2 hr
  4. temperatureand then cooled (ice bath)
  5. temperatureThe mixture is heated
  6. temperatureunder reflux for 15 minutes
  7. temperaturecooled
  8. filtrationThe mixture is filtered
  9. washwashing well with ether
  10. customThe ether solution is collected
  11. extractionextracted with chloroform
  12. customevaporated

Sources & evidence

ORD record
ord-7606d95e6e4547c493519878476e2c4e
Source dataset
uspto-grants-1977_07
Patent number
US04036842

Reaction notes

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