Ammonia → HCID 68886568, compound

HRID 1864609Notes

Reaction equation

HRID 1864609 reaction equation
Cl[C:2]1[C:15]2[CH:14]=[C:13]3[C:8]([CH:9]=[CH:10][CH:11]=[N:12]3)=[CH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.N.[CH3:17][N:18](C)C(=O)C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].[Zn].[C-]#N.[C-]#N.[Zn+2]>[C:17]([C:2]1[C:15]2[CH:14]=[C:13]3[C:8]([CH:9]=[CH:10][CH:11]=[N:12]3)=[CH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1)#[N:18]

Participants

8

Reactant 3

HCID 222AmmoniaHCID 31374DimethylacetamideHCID 68887137HCID 68887137, compound

Product 1

HCID 68886568HCID 68886568, compoundYield 91%

Reagents, catalysts & solvents 4

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 23994ZincCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

A N,N-dimethylacetamide (110 mL) solution of the 9-chlorobenzo[g]quinoline (10.8 g, 55.27 mmol) from Step 2, Pd2(dba)3 (1.02 g, 0.02 eq), dppf (1.25 g, 0.04 eq), Zn powder (0.457 g, 0.13 eq) and Zn(CN)2 (3.97 g, 0.61 eq) was heated at 150° C. for 8 h in a sealed tube. The mixture was then poured into aqueous ammonia (2 N, 500 mL). The resulting yellow precipitate was collected by filtration and redissolved in CH2Cl2. The filtrate was extracted once with ethyl acetate. The organic phase was combined, dried over MgSO4, filtered and concentrated to ˜10% of original solvent volume. Pure 9-cyanobenzo[g]quinoline (10.3g, 91%) was obtained by filtration. MS Found: (M+H)+=205.

Workup

  1. filtrationThe resulting yellow precipitate was collected by filtration
  2. dissolutionredissolved in CH2Cl2
  3. extractionThe filtrate was extracted once with ethyl acetate
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to ˜10% of original solvent volume

Sources & evidence

ORD record
ord-4b1050b3e2584759bf4d24620dd48dd5
Source dataset
uspto-grants-2009_12
Patent number
US07625921B2

Reaction notes

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