Hydrochloric Acid → HCID 178485493, compound

HRID 1378336Notes

Reaction equation

HRID 1378336 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]2[C:3]=1[C:4](=[N:17][S:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:20])=[O:19])[CH:5]=[C:6]([C:13]([O:15]C)=O)[NH:7]2.[CH3:27][NH2:28].Cl>O.O1CCOCC1>[CH3:27][NH:28][C:13]([C:6]1[NH:7][C:8]2[C:3]([C:4](=[N:17][S:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)(=[O:19])=[O:20])[CH:5]=1)=[C:2]([Cl:1])[CH:11]=[C:10]([Cl:12])[CH:9]=2)=[O:15]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 178498474HCID 178498474, compound

Product 1

HCID 178485493HCID 178485493, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

Combine 5,7-dichloro-4-[benzenesulfonylimino]-1,4-dihydroquinoline-2-carboxylic acid, methyl ester (1.0 g, 2.4 mmol) and 40% methylamine in water (25 mL) and dioxane (50 mL). Stopper and stir for 18 hours. Evaporate in vacuo to give a yellow oil. Dissolve the oil in water (15 mL) and add 1M hydrochloric acid solution (15 mL). Stir for 15 minutes and then filter to obtain a solid. Rinse the solid with 1M hydrochloric acid solution and water. Recrystallize from acetonitrile/water to give the title compound as a solid: mp; 196°-197° C. Elem. Anal. calculated for C17H13Cl2N3O3S.H2O: C, 47.68; H, 3.53; N, 9.81. Found: C, 47.55; H, 3.42; N, 9.78.

Workup

  1. customEvaporate in vacuo
  2. customto give a yellow oil
  3. stirringStir for 15 minutes
  4. filtrationfilter
  5. customto obtain a solid
  6. washRinse the solid with 1M hydrochloric acid solution and water
  7. customRecrystallize from acetonitrile/water

Sources & evidence

ORD record
ord-25c5032ce3ec46b09c25b3f548b39bb6
Source dataset
uspto-grants-1997_09
Patent number
US05668143

Reaction notes

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