Tetrahydrofuran → HCID 178510287, compound

HRID 989317Notes

Reaction equation

HRID 989317 reaction equation
[SH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:22])[C:7]([C:20]#[N:21])=[CH:8][N:9]2COCC[Si](C)(C)C)=[CH:4][C:3]=1[N+:23]([O-])=O.O1CCC[CH2:27]1>CO>[OH:22][C:6]1[C:5]2[CH:4]=[C:3]3[N:23]=[CH:27][S:1][C:2]3=[CH:11][C:10]=2[N:9]=[CH:8][C:7]=1[C:20]#[N:21]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 21956425HCID 21956425, compound

Product 1

HCID 178510287HCID 178510287, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 377 mg (1.0 mmol) of 1,4-dihydro-7-mercapto-6-nitro-4-oxo-1-[[2-(trimethylsilyl)ethoxy]methyl]-3-quinolinecarbonitrile and 200 mg of 20% palladium-hydroxide-on-carbon in 50 mL of tetrahydrofuran and 10 mL of methanol is hydrogenated in a Parr apparatus at 40 psi for 30 minutes. The mixture is filtered and concentrated in vacuo. The residue is dissolved in 5 mL of 98% formic acid, and 200 mg of imidazole is added to the solution. The solution is refluxed for 2 hours and cooled to room temperature. To this solution is added a mixture of 100 mL ethyl acetate and 50 mL of hexanes. The solids thus formed are filtered, washed with ethyl acetate, and dried to yield 125 mg (55%) of a tan solid, mp 200° C. (decomposed).

Workup

  1. filtrationThe mixture is filtered
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue is dissolved in 5 mL of 98% formic acid
  4. addition200 mg of imidazole is added to the solution
  5. temperatureThe solution is refluxed for 2 hours
  6. additionTo this solution is added
  7. additiona mixture of 100 mL ethyl acetate and 50 mL of hexanes
  8. customThe solids thus formed
  9. filtrationare filtered
  10. washwashed with ethyl acetate
  11. customdried

Sources & evidence

ORD record
ord-d9af6d5485cf4f76906bcdfefa169d09
Source dataset
uspto-grants-2003_10
Patent number
US06638929B2

Reaction notes

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