Hydrochloric Acid → HCID 58380528, compound

HRID 1259386Notes

Reaction equation

HRID 1259386 reaction equation
Cl.Cl[Sn]Cl.O.[F:6][C:7]1[CH:12]=[C:11]([I:13])[CH:10]=[CH:9][C:8]=1[NH:14][C:15]1[C:16]([N+:26]([O-])=O)=[C:17]2[O:25][CH2:24][CH2:23][N:18]2[C:19](=[O:22])[C:20]=1[CH3:21].C(=O)(O)[O-]>C(O)C.C(OC(=O)C)C>[NH2:26][C:16]1[C:15]([NH:14][C:8]2[CH:9]=[CH:10][C:11]([I:13])=[CH:12][C:7]=2[F:6])=[C:20]([CH3:21])[C:19](=[O:22])[N:18]2[CH2:23][CH2:24][O:25][C:17]=12

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 769Bicarbonate IonHCID 43835034Tin dichloride dihydrateHCID 583805937-(2-Fluoro-4-iodo-phenylamino)-6-methyl-8-nitro-2,3-dihydro-oxazolo[3,2-a]pyridin-5-one

Product 1

HCID 58380528HCID 58380528, compoundYield 57.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

Concentrated HCl (0.2 mL) and SnCl2.H2O (0.24 g, 1.06 mmol) were added to 7-(2-fluoro-4-iodo-phenylamino)-6-methyl-8-nitro-2,3-dihydro-oxazolo[3,2-a]pyridin-5-one (0.15 g, 0.347 mmol) in ethanol (5 mL). The resulting mixture was heated to reflux for 2 hours. The reaction was monitored by TLC (100% ethylacetate). The reaction mixture was cooled to room temperature, diluted with ethylacetate, basified with saturated bicarbonate solution and filtered through celite. The organic layer was washed with brine solution, dried over Na2SO4 and concentrated to afford 0.08 g of the crude product which was used in the next step without further purification.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 2 hours
  3. filtrationfiltered through celite
  4. washThe organic layer was washed with brine solution
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-591d17101e174c3aa9559ebfca0581dc
Source dataset
uspto-grants-2013_06
Patent number
US08466289B2

Reaction notes

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