Ammonia → HCID 20150452, compound

HRID 568348Notes

Reaction equation

HRID 568348 reaction equation
O.O.[Na].[Na].[C:5]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:15]=[C:16]3[C:21](=[CH:22][CH:23]=2)[NH:20][C:19](=[O:24])[CH:18]=[CH:17]3)=[CH:10][CH:9]=1)(O)=[O:6].[NH3:25]>S(Cl)(Cl)=O>[C:5]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:15]=[C:16]3[C:21](=[CH:22][CH:23]=2)[NH:20][C:19](=[O:24])[CH:18]=[CH:17]3)=[CH:10][CH:9]=1)(=[O:6])[NH2:25]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 131715459HCID 131715459, compound

Product 1

HCID 20150452HCID 20150452, compound

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

A suspension of 6-[4-carboxyphenyl]-2-(1H)-quinolone disodium salt dihydrate (0.5 g) (see Example 13B) in thionyl chloride (10 cm3) was heated under reflux for 10 minutes. The cooled solution was evaporated in vacuo to afford a yellow solid which was treated without purification with aqueous ammonia solution (5 cm3, S.G. 0.88) with stirring. The solid material was filtered off and warmed with chloroform:methanol, 4:1, to remove soluble impurities and the remaining solid was filtered to afford the title compound, m.p. >320°, (0.3 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 10 minutes
  3. customThe cooled solution was evaporated in vacuo
  4. customto afford a yellow solid which
  5. filtrationThe solid material was filtered off
  6. temperaturewarmed with chloroform
  7. custommethanol, 4:1, to remove soluble impurities
  8. filtrationthe remaining solid was filtered

Sources & evidence

ORD record
ord-27983269fd9a4fdc9892fe31e7fcf512
Source dataset
uspto-grants-1988_03
Patent number
US04728654

Reaction notes

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