Hydrochloric Acid → HCID 59749552, compound

HRID 747274Notes

Reaction equation

HRID 747274 reaction equation
C(=[N:14][CH:15]([CH:18]([C:20]1[CH:29]=[CH:28][CH:27]=[C:26]2[C:21]=1[CH:22]=[CH:23][CH:24]=[N:25]2)[CH3:19])[C:16]#[N:17])(C1C=CC=CC=1)C1C=CC=CC=1.Cl>O1CCOCC1>[NH2:14][CH:15]([CH:18]([C:20]1[CH:29]=[CH:28][CH:27]=[C:26]2[C:21]=1[CH:22]=[CH:23][CH:24]=[N:25]2)[CH3:19])[C:16]#[N:17]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86604124HCID 86604124, compound

Product 1

HCID 59749552HCID 59749552, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2-(Benzhydrylidene-amino)-3-quinolin-5-yl-butyronitrile (8.36 g, 22.3 mmol) in dioxane (90 mL) was hydrolyzed with 1M HCl (90 mL) and the solution was stirred at rt for 16 h. The dioxane was removed under vacuum and the mixture was made basic with 2 M NaOH. The aqueous solution was extracted with chloroform:isopropanol (3:1). The organic extracts were pooled, dried over MgSO4, filtered and evaporated to leave an oil. The oily residue was purified by chromatography on SiO2, eluting with ethyl acetate and 5% methanol:ethyl acetate to give 2-amino-3-quinolin-5-yl-butyronitrile (Intermediate-E2) as a yellow solid 3.61 g (77%).

Workup

  1. customThe dioxane was removed under vacuum
  2. extractionThe aqueous solution was extracted with chloroform:isopropanol (3:1)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customto leave an oil
  7. customThe oily residue was purified by chromatography on SiO2
  8. washeluting with ethyl acetate and 5% methanol

Sources & evidence

ORD record
ord-0987dcb7dd7a4660aa51a48065ce0b2e
Source dataset
uspto-grants-2008_07
Patent number
US07396849B2

Reaction notes

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