Sulfuric Acid → HCID 23369593, compound

HRID 1900725Notes

Reaction equation

HRID 1900725 reaction equation
[N:1]([CH2:4][CH:5]1[O:20][C:8]2=[C:9]3[C:14](=[C:15]([C:17]#[N:18])[CH:16]=[C:7]2[CH2:6]1)[NH:13][C:12](=[O:19])[CH:11]=[CH:10]3)=[N+:2]=[N-:3].S(=O)(=O)(O)[OH:22].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[N:1]([CH2:4][CH:5]1[O:20][C:8]2=[C:9]3[C:14](=[C:15]([C:17](=[O:22])[NH2:18])[CH:16]=[C:7]2[CH2:6]1)[NH:13][C:12](=[O:19])[CH:11]=[CH:10]3)=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 11430Potassium CarbonateHCID 23369626HCID 23369626, compound

Product 1

HCID 23369593HCID 23369593, compoundYield 6.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Azidomethyl-5-cyano-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one (3.4 g) was suspended in 95% ethanol (85 ml). Concentrated sulfuric acid (32 ml) was added to the mixture, and the mixture was refluxed for 5 hours while heating. 30% potassium carbonate was added to the reaction mixture to turn the pH of the mixture alkaline. Extraction was performed using a solvent mixture of chloroform-methanol (8:1), and the extract was dried. The solvent was distilled off, and the resultant residue was washed with chloroform to obtain 0.232 g of 2-azidomethyl-5-carbamoyl -2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one as a pale brown solid (6.4%, mp.: 220°-223° C. (dec.)). The chloroform used to wash the above-described residue was dried to solidity under reduced pressure, and the obtained crude product was purified by silica gel column chromatography (eluent=chloroform) to obtain 1.64 g of 2-azidomethyl-5-ethoxycarbonyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one (41.1%). The purified product was recrystallized from acetone to obtain colorless needles (mp.: 173° C.).

Workup

  1. temperaturethe mixture was refluxed for 5 hours
  2. temperaturewhile heating
  3. extractionExtraction
  4. additiona solvent mixture of chloroform-methanol (8:1)
  5. customthe extract was dried
  6. distillationThe solvent was distilled off
  7. washthe resultant residue was washed with chloroform

Sources & evidence

ORD record
ord-d07f78a3771143d986e345fe232ab2fa
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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