Dimethylformamide → 4-Chloroquinoline-6-carbonitrile

HRID 503602Notes

Reaction equation

HRID 503602 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9](I)[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[CH3:13][N:14](C=O)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C-]#N.[Zn+2].[C-]#N>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:13]#[N:14])[CH:10]=2)[N:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 111737784-Chloro-6-iodoquinoline

Product 1

HCID 204935814-Chloroquinoline-6-carbonitrile

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
50 °C

Procedure

A pyrex reaction tube was charged with Pd(PPh3)4(200 mg, 173 μmol), 4-chloro-6-iodoquinoline (1.00 g, 3454 μmol), zinc cyanide (406 mg, 3454 μmol) and DMF. The tube was purged with argon, sealed, and the heterogeneous mixture was stirred at 50° C. for 17 h. The mixture was poured into water and the resulting solids were filtered, washed with water, and dried. The crude material was purified by silica gel chromatography, 0-5% MeOH/DCM to provide 4-chloroquinoline-6-carbonitrile as a white solid. MS: [M+H]=189.

Workup

  1. customThe tube was purged with argon
  2. customsealed
  3. additionThe mixture was poured into water
  4. filtrationthe resulting solids were filtered
  5. washwashed with water
  6. customdried
  7. customThe crude material was purified by silica gel chromatography, 0-5% MeOH/DCM

Sources & evidence

ORD record
ord-092274b21db340df9e9bd441640bf92c
Source dataset
uspto-grants-2010_08
Patent number
US07776857B2

Reaction notes

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