Dimethylformamide → HCID 22170220, compound

HRID 1822858Notes

Reaction equation

HRID 1822858 reaction equation
Cl[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:16]([NH2:18])=[O:17].C[N:20]([CH:22]=O)C>C(O)(=O)C>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH3:15])[N:5]=[CH:4][C:3]([C:16]([NH2:18])=[O:17])=[C:2]2[NH:20][C:22]1[CH:4]=[CH:3][CH:2]=[CH:11][C:10]=1[CH2:9][CH2:8][CH3:7]

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 221702044-Chloro-6,7-dimethoxyquinoline-3-carboxamide

Product 1

HCID 22170220HCID 22170220, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 4-chloro-6,7-dimethoxy-3-quinolinecarboxamide (0.062 g, 0.23 mmol) 2-propylanilin (0.038 g, 0.28 mmol), 2-butanole (2 ml), DMF (2 ml) and acetic acid (8.2 μl) was heated over night at 100 C. After cooling, the solution was reduced by evaporation. The residue was dissolved in water (3 ml) and treated with aqueous ammonia. The solid product was filtered off washed with water air dried for 0.5 h, washed again with heptane and dried in a vacuum oven at 50 C. to give a yellow-brown solid, 35 mg (41%) of the title compound. APCI-LC/MS m/z 366.1 (MH+): 1H NMR (DMSO-d6) δ 10.95 (1H, s); 8.88 (1H, s); 8.28 (1H, br s); 7.62 (1H, br s); 7.29 (1H, m); 7.24 (1H, s); 7.05 (2H, m); 6.68 (1H, m); 6.63 (1H, s); 3.88 (3H, s); 3.21 (3H, s); 2.67 (2H, t); 1.65 (2H, m); 0.93 (3H, t).

Workup

  1. temperaturewas heated over night at 100 C
  2. temperatureAfter cooling
  3. customthe solution was reduced by evaporation
  4. dissolutionThe residue was dissolved in water (3 ml)
  5. additiontreated with aqueous ammonia
  6. filtrationThe solid product was filtered off
  7. washwashed with water air
  8. customdried for 0.5 h
  9. washwashed again with heptane
  10. customdried in a vacuum oven at 50 C

Sources & evidence

ORD record
ord-8dd95f8dfbcc4826a6572d61ac555d71
Source dataset
uspto-grants-2006_05
Patent number
US07037925B2

Reaction notes

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