Hydrochloric Acid → Ethyl 6-amino-8-methoxycarbonyl-4-oxo-10-propyl-4H-pyrano[3,2-g]quinoline-2-carboxylate

HRID 65493Notes

Reaction equation

HRID 65493 reaction equation
ClC1C=CC(OS([N:10]=C=O)(=O)=O)=CC=1.[O:15]=[C:16]1[C:21]2[CH:22]=[C:23]3[C:28](=[C:29]([CH2:30][CH2:31][CH3:32])[C:20]=2[O:19][C:18]([C:38]([O:40][CH2:41][CH3:42])=[O:39])=[CH:17]1)[NH:27][C:26]([C:33]([O:35][CH3:36])=[O:34])=[CH:25][C:24]3=O.Cl>C(#N)C>[NH2:10][C:24]1[C:23]2[C:28](=[C:29]([CH2:30][CH2:31][CH3:32])[C:20]3[O:19][C:18]([C:38]([O:40][CH2:41][CH3:42])=[O:39])=[CH:17][C:16](=[O:15])[C:21]=3[CH:22]=2)[N:27]=[C:26]([C:33]([O:35][CH3:36])=[O:34])[CH:25]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 113792984-ChlorophenoxysulphonylisocyanateHCID 13101142Ethyl 6,9-dihydro-4,6-dioxo-8-methoxycarbonyl-10-propyl-4H-pyrano[3,2-g]quinoline-2-carboxylate

Product 1

HCID 13544003Ethyl 6-amino-8-methoxycarbonyl-4-oxo-10-propyl-4H-pyrano[3,2-g]quinoline-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Chlorophenoxysulphonylisocyanate (0.2 ml, 290 mg) was added to a suspension of ethyl 6,9-dihydro-4,6-dioxo-8-methoxycarbonyl-10-propyl-4H-pyrano[3,2-g]quinoline-2-carboxylate (385 mg, 1 mmol) in acetonitrile (5 ml), and then refluxed for 0.5 h. The solution was allowed to cool, ethanolic hydrogen chloride solution (2 ml) was added, and after 5 minutes the pale yellow solution was poured into aqueous ammonial solution (0.88 specific gravity, 5 ml) at 5° C., to give a thick orange precipitate. Filtration and washing with ethanol (10 ml) gave the title compound, 320 mg (83%) as an orange powder, mp 268°-270° C. (decomposes).

Workup

  1. temperaturerefluxed for 0.5 h
  2. temperatureto cool
  3. additionafter 5 minutes the pale yellow solution was poured into aqueous ammonial solution (0.88 specific gravity, 5 ml) at 5° C.
  4. customto give a thick orange precipitate
  5. filtrationFiltration
  6. washwashing with ethanol (10 ml)

Sources & evidence

ORD record
ord-1b7e2365c17a49688ebb996578f31e0d
Source dataset
uspto-grants-1986_09
Patent number
US04614802

Reaction notes

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