Sodium Chloride → HCID 117992061, compound

HRID 589013Notes

Reaction equation

HRID 589013 reaction equation
[Cl-].[Na+].[OH:3][C:4]1[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[CH2:8][CH:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[O:6][C:5]=1C(OC)=O>CS(C)=O.O>[C:15]1([CH:7]2[O:6][CH2:5][C:4](=[O:3])[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[CH2:8]2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 2

HCID 5234Sodium ChlorideHCID 117992043HCID 117992043, compound

Product 1

HCID 117992061HCID 117992061, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

Sodium chloride (0.10 g, 1.7 mmol) was added to a solution of methyl 9-hydroxy-6-phenyl-5,6-dihydrooxepino[4,5-b]pyridine-8-carboxylate (0.50 g, 1.7 mmol) in dimethylsulfoxide (8 mL) and water (0.4 mL). The resulting mixture was heated at 150° C. for 2 h, then cooled and partitioned between water and ethyl acetate (3×). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by flash chromatography on silica gel eluting with 40% ethyl acetate in petroleum ether to give the title compound. MS: m/z=240.0 (M+1).

Workup

  1. temperaturecooled
  2. custompartitioned between water and ethyl acetate (3×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography on silica gel eluting with 40% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-9b763612f4d24eaebb0f6ffdb73ea722
Source dataset
uspto-grants-2016_01
Patent number
US09227973B2

Reaction notes

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