Hydrochloric Acid → HCID 67026411, compound

HRID 520273Notes

Reaction equation

HRID 520273 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1C(Cl)=O.[NH2:9][C:10]1[CH:11]=[N:12][C:13]2[C:18]([C:19]=1[NH2:20])=[CH:17][CH:16]=[CH:15][CH:14]=2.O.Cl.Cl[CH2:24]Cl>N1C=CC=CC=1.[OH-].[Na+]>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[N:20]1[C:19]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:12]=[CH:11][C:10]=2[N:9]=[CH:24]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 6344DichloromethaneHCID 682422-Furancarbonyl chlorideHCID 15142893,4-Diaminoquinoline

Product 1

HCID 67026411HCID 67026411, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 14798Sodium HydroxideSolvent

Procedure

2-Furoyl chloride (1.1 g, 0.8 ml, 8.1 mmol) in dry dichloromethane (15 ml) was added dropwise to a solution of to 3,4-diaminoquinoline 8 (1.0 g, 6.0 mmol) in dry pyridine (6.2 ml) under nitrogen. The solution was stirred for 2 hours at room temperature. Water (15 ml) was added to quench the reaction and the solvent was evaporated under reduced pressure to afford an orange solid. This crude solid in 2N NaOH (15 ml) was refluxed for 2 hours. After cooling on ice the pH was adjusted to 7 using concentrated HCl. The solid that precipitated was filtered off and washed with water and ether. Then extracted with ethyl acetate (3 times 15 ml) and washed with water (3 time 15 ml) and dried over MgSO4. The solvent was evaporated and the residue was dried. Eluent for column chromatography was 1-5% methanol in dichloromethane. Yield: 0.62 g (44%). Mp.: 236-238° C. 1H NMR (DMSO-d6): δ 6.74 (s, 1H, Ar); 7.35 (d, 1H, J=3.7 Hz, Ar); 7.69-7.73 (m, 2H, Ar); 7.83 (s, 1H, Ar); 8.09 (s, 1H, Ar); 8.46 (s, 1H, Ar); 9.09 (s, 1H, Ar). 13C NMR (DMSO-d6): δ 111.4, 112.6, 120.7, 121.8, 126.5, 127.2, 129.5, 138.2, 143.6, 144.3, 145.1, 147.2, 155.4.

Workup

  1. customto quench
  2. customthe reaction
  3. customthe solvent was evaporated under reduced pressure
  4. customto afford an orange solid
  5. temperatureAfter cooling on ice the pH
  6. customThe solid that precipitated
  7. filtrationwas filtered off
  8. washwashed with water and ether
  9. extractionThen extracted with ethyl acetate (3 times 15 ml)
  10. washwashed with water (3 time 15 ml)
  11. dry with materialdried over MgSO4
  12. customThe solvent was evaporated
  13. customthe residue was dried

Sources & evidence

ORD record
ord-72423cc481cc4f3d9e10c9925f7fd0f3
Source dataset
uspto-grants-2016_05
Patent number
US09326978B2

Reaction notes

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