Dimethylformamide → 4-Chloro-6,7-dimethoxyquinoline-3-carboxamide

HRID 2115817Notes

Reaction equation

HRID 2115817 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1I.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C[N:47]([CH:49]=[O:50])C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:49]([NH2:47])=[O:50]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 812191,3-Bis(diphenylphosphino)propaneHCID 67520363HCID 67520363, compound

Product 1

HCID 221702044-Chloro-6,7-dimethoxyquinoline-3-carboxamide

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Conditions

Temperature
100 °C

Procedure

A stainless steel cylinder was charged with 4-chloro-3-iodo-6,7-dimethoxyquinoline (0.200 g, 0.572 mmol), palladium(II) acetate (0.013 g, 0.057 mmol), 1,3-bis(diphenylphosphino)propane (0.047 g, 0.11 mmol), DMF (2 mL), and 1,1,1,3,3,3-hexamethyldisilazane S (0.37 g, 0.48 mL, 2.3 mmol). The cylinder was sealed and pressurized with CO gas at 30 psi. The system was heated at 100° C. for 1.5 h and then cooled to RT. The mixture was concentrated to afford an orange solid. This material was triturated with dichloromethane and the resulting precipitate was filtered and dried to afford 4-chloro-6,7-dimethoxyquinoline-3-carboxamide as an off-white solid. MS (ESI, pos. ion) m/z: 267.0 (M+H). Mass Calc'd for C12H11ClN2O3: 266.

Workup

  1. customThe cylinder was sealed
  2. temperaturecooled to RT
  3. concentrationThe mixture was concentrated
  4. customto afford an orange solid
  5. customThis material was triturated with dichloromethane
  6. filtrationthe resulting precipitate was filtered
  7. customdried

Sources & evidence

ORD record
ord-b084fa3913e44ce28b71868a07cd0c5c
Source dataset
uspto-grants-2008_10
Patent number
US07435823B2

Reaction notes

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