Hydrochloric Acid → HCID 20478434, compound

HRID 904684Notes

Reaction equation

HRID 904684 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]3[O:15][C:14]([C:16]([O:18]CC)=[O:17])=[CH:13][C:12](=[O:21])[C:10]3=2)[N:5]=[C:4]([C:22]([O:24]C)=[O:23])[CH:3]=1.[OH-].[Na+].Cl>CO>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]3[O:15][C:14]([C:16]([OH:18])=[O:17])=[CH:13][C:12](=[O:21])[C:10]3=2)[N:5]=[C:4]([C:22]([OH:24])=[O:23])[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 20478449HCID 20478449, compound

Product 1

HCID 20478434HCID 20478434, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl methyl 10-chloro-1-oxo-1H-pyrano[3,2-f]quinoline-3,8-dicarboxylate (300 mg; 0.83 mmole) in methanol (30 ml) was heated under reflux during the dropwise addition of M/10 aqueous sodium hydroxide (16.6 ml; 1.66 mmole) with stirring over 1.5 hrs. After the addition the mixture was heated under reflux for a further 2 hrs when it was cooled and poured into dilute aqueous hydrochloric acid. The brown solid was filtered off and dried in a vacuum oven over sodium hydroxide pellets. This gave analytically pure title compound 210 mg (79%) (decomp. 253°). NNMR (d6DMSO) δ, 8.48, 8.13 (AB quartet, J=9H); δ, 8.33 (s,1H), 7.2 (s, 1H).

Workup

  1. additionAfter the addition the mixture
  2. temperaturewas heated
  3. temperatureunder reflux for a further 2 hrs when it
  4. temperaturewas cooled
  5. filtrationThe brown solid was filtered off
  6. dry with materialdried in a vacuum oven over sodium hydroxide pellets

Sources & evidence

ORD record
ord-4152c3a9eb414c619cb4c4f599893ab7
Source dataset
uspto-grants-1983_12
Patent number
US04419352

Reaction notes

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