Ammonia → 8-Bromoquinoline-5-carbonitrile

HRID 1017127Notes

Reaction equation

HRID 1017127 reaction equation
Cl.N[C:3]1[CH:12]=[CH:11][C:10]([Br:13])=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[N:8]2.N([O-])=O.[Na+].[NH2:18][C:19](N)=O.C1(C)C=CC=CC=1.[Cu]C#N.N.[C-]#N.[Na+]>O.S([O-])([O-])(=O)=O.[Cu+2].C1(C)C=CC=CC=1.C(O)(=O)C>[Br:13][C:10]1[CH:11]=[CH:12][C:3]([C:19]#[N:18])=[C:4]2[C:9]=1[N:8]=[CH:7][CH:6]=[CH:5]2

Participants

12

Reactant 7

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 1176UreaHCID 8929Sodium CyanideHCID 129500548-Bromoquinolin-5-amineHCID 23668193Sodium NitriteHCID 178424363HCID 178424363, compound

Product 1

HCID 184030268-Bromoquinoline-5-carbonitrile

Reagents, catalysts & solvents 4

HCID 24462Copper SulfateCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent3×HCID 1140TolueneSolvent

Procedure

0.60 g of concentrated hydrochloric acid was added dropwise to a mixture of 0.70 g of 5-amino-8-bromoquinoline and 3.15 ml of acetic acid, and the mixture was stirred for 1 hour at room temperature. At 0-5° C., 0.22 g of sodium nitrite in 0.45 ml of water were then added, and the mixture was stirred for 1 hour. After the addition of 20 mg of urea in 0.16 ml of water, stirring was continued at 0-5° C. for a further hour. This solution is added to a two-phase system of toluene/copper(I) cyanide solution which was prepared as follows: a solution of 0.79 g of copper(II) sulfate in 2.2 ml of water was added dropwise to a solution of 1.06 g of 10% strength ammonia solution and 0.77 g of sodium cyanide, and 6 ml of toluene were added to this mixture to form a lower layer. After stirring for 1 hour at room temperature, insoluble particles were filtered off and the solution was extracted with ethyl acetate. The organic phase was dried and the solvent was removed under reduced pressure.

Workup

  1. stirringthe mixture was stirred for 1 hour
  2. stirringstirring
  3. waitwas continued at 0-5° C. for a further hour
  4. customwas prepared
  5. additionwere added to this mixture
  6. customto form a lower layer
  7. stirringAfter stirring for 1 hour at room temperature
  8. filtrationinsoluble particles were filtered off
  9. extractionthe solution was extracted with ethyl acetate
  10. customThe organic phase was dried
  11. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-a749916fcb3e41b6ae924cdd07eeccaa
Source dataset
uspto-grants-2002_11
Patent number
US06479436B1

Reaction notes

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