Reaction #6910

ord-410a6f1443c34331ba6735f7cc64c911

Reaction equation

CC(C)(C)C(=O)NC1CCN(c2ccc3cc(C#N)ccc3n2)C1
product
CC(C)(C)C(=O)NC1CCN(c2ccc3cc(C#N)ccc3n2)C1
N-[1-(6-cyanoquinolin-2-yl)pyrrolidin-3-yl]-2,2-dimethylpropanamide
Cl.NO
hydroxyl amine hydrochloride
O=C([O-])[O-].[Na+].[Na+]
sodium carbonate
→
CC(C)(C)C(=O)NC1CCN(c2ccc3cc(C(=N)NO)ccc3n2)C1
N-(1-{6-[(Hydroxyamino)(imino)methyl]quinolin-2-yl}pyrrolidin-3-yl)-2,2-dimethylpropanamide

Reactants

CC(C)(C)C(=O)NC1CCN(c2ccc3cc(C#N)ccc3n2)C1
product
CC(C)(C)C(=O)NC1CCN(c2ccc3cc(C#N)ccc3n2)C1
N-[1-(6-cyanoquinolin-2-yl)pyrrolidin-3-yl]-2,2-dimethylpropanamide
Cl.NO
hydroxyl amine hydrochloride
O=C([O-])[O-].[Na+].[Na+]
sodium carbonate

Reagents

None

Solvents

ClCCl
dichloromethane
O
water
CCO
ethanol

Conditions

Temperature
90°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Washwashed twice with brine
  2. 2
    Dryingdried over sodium sulfate
  3. 3
    Filtrationfiltered through a fritted funnel
  4. 4
    Otherthe volatiles were removed under vacuum
  5. 5
    OtherThis provided the product, MS
  6. 6
    Otherm/z 356, which was used in the next step without further purification

Procedure

A mixture of the product of Step D (60 mg; 0.1863 mmol), hydroxyl amine hydrochloride (3 eq.), sodium carbonate (4 eq.) in 1.5 mL water and 2.5 mL ethanol was heated to 90° C. for 6 h. The mixture was diluted with dichloromethane, washed twice with brine, dried over sodium sulfate, filtered through a fritted funnel and the volatiles were removed under vacuum. This provided the product, MS: m/z 356, which was used in the next step without further purification.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07084156B2uspto-grants-2006_08