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

HRID 1925313Notes

Reaction equation

HRID 1925313 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 Cl2H11ClN2O3: 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-4736416b7b8d410488cd40e9a7353f31
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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