Ethanol → HCID 59003053, compound

HRID 561115Notes

Reaction equation

HRID 561115 reaction equation
[NH2:1][C:2]1[C:11]([F:12])=[C:10]([NH:13][CH2:14][CH2:15][NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)[C:9]([O:23][CH3:24])=[C:8]2[C:3]=1[C:4](=[O:31])[C:5]([C:28]([OH:30])=[O:29])=[CH:6][N:7]2[CH:25]1[CH2:27][CH2:26]1.OS(O)(=O)=O.C([O-])(O)=O.[Na+].[CH3:42][CH2:43]O>>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([NH:13][CH2:14][CH2:15][NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)[C:9]([O:23][CH3:24])=[C:8]2[C:3]=1[C:4](=[O:31])[C:5]([C:28]([O:30][CH2:42][CH3:43])=[O:29])=[CH:6][N:7]2[CH:25]1[CH2:27][CH2:26]1

Participants

5

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 24754025HCID 24754025, compound

Product 1

HCID 59003053HCID 59003053, compoundYield 44%

Procedure

A mixture of 5-Amino-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-7-[2-(2-pyridylamino)ethylamino]quinoline-3-carboxylic acid (428 mg, 1.00 mmol) and concentrated H2SO4 (1.0 mL) in EtOH (15 mL) was refluxed for 8 h. After cooling, the mixture was poured into ice water (100 mL). Saturated aq. NaHCO3 (50 mL) was added and the crude product was extracted with CH2Cl2 (2×50 mL). The extraction mixture washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography (Chromatorex NH-DM2035 (Fuji Sylysia Chemical Co., Ltd.), EtOAc) to give ethyl 5-amino-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-7-[2-(2-pyridylamino)ethylamino]quinoline-3-carboxylate (311 mg, 44%) as a pale yellow solid.

Workup

  1. temperaturewas refluxed for 8 h
  2. temperatureAfter cooling
  3. extractionthe crude product was extracted with CH2Cl2 (2×50 mL)
  4. washThe extraction mixture washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (Chromatorex NH-DM2035 (Fuji Sylysia Chemical Co., Ltd.), EtOAc)

Sources & evidence

ORD record
ord-061c2d03b60446f38479a14a24a7379d
Source dataset
uspto-grants-2011_11
Patent number
US08063221B2

Reaction notes

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