Water → HCID 10797085, compound

HRID 428178Notes

Reaction equation

HRID 428178 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH:3]=[C:2]1[C:11]#[N:12].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>CCOCC>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH:3]=[C:2]1[CH2:11][NH2:12]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 105111471,4-Benzodioxin-2-carbonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 10797085HCID 10797085, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1 g (6.29 mmol) of the nitrile obtained in Step A is dissolved in 50 ml of anhydrous ether; 0.31 g (8.17 mmol) of lithium aluminium hydride is then added very slowly to the solution. After 3 hours of reflux under argon, the reaction medium is returned to ambient temperature and then hydrolysed with, in succession, 0.31 ml of water, 0.31 ml of a 15% sodium hydroxide solution and 0.93 ml of water. After 30 minutes of stirring at ambient temperature, the salts are filtered off; the filtrate is then dried over magnesium sulphate. The filtered organic phase is concentrated in vacuo to yield the title amine in the form of a yellow oil.

Workup

  1. temperatureAfter 3 hours of reflux under argon
  2. customis returned to ambient temperature
  3. filtrationthe salts are filtered off
  4. dry with materialthe filtrate is then dried over magnesium sulphate
  5. concentrationThe filtered organic phase is concentrated in vacuo

Sources & evidence

ORD record
ord-a007bc9bd5e148f892f3d63cc932ed45
Source dataset
uspto-grants-2001_11
Patent number
US06313160B1

Reaction notes

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