Water → HCID 12873132, compound

HRID 525899Notes

Reaction equation

HRID 525899 reaction equation
[Cl-:1].[C:2]([C:5]1[C:14](=[O:15])[C:13]2[C:12]([N+]#N)=[C:11]3[O:18]C[O:20][C:10]3=[CH:9][C:8]=2[N:7]([CH2:21][CH3:22])[CH:6]=1)([OH:4])=[O:3].O>OS(O)(=O)=O>[Cl:1][C:12]1[C:11]([OH:18])=[C:10]([OH:20])[CH:9]=[C:8]2[C:13]=1[C:14](=[O:15])[C:5]([C:2]([OH:4])=[O:3])=[CH:6][N:7]2[CH2:21][CH3:22]

Participants

4

Reactant 2

HCID 962WaterHCID 12873126HCID 12873126, compound

Product 1

HCID 12873132HCID 12873132, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 7-carboxy-5-ethyl-8-oxo-5,8-dihydro-[1,3]dioxolo[4,5-g]quinoline-9-diazonium chloride (7.5 g, 23.17 mmol) (Mixture of 16c and 16d) in 50% H2SO4 (60 mL) was heated at 95° C. for 4 h. The reaction mixture was cooled down to r.t. and then poured into 450 mL of water. The precipitates were collected by filtration and dried to afford 5-chloro-1-ethyl-6,7-dihydroxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (6 g, 18.61 mmol, 80% yield) as a yellow brown solid. LCMS: (M+H)+: 284.1.

Workup

  1. filtrationThe precipitates were collected by filtration
  2. customdried

Sources & evidence

ORD record
ord-cd77808fc5184d82b273ad4e5a986b21
Source dataset
uspto-grants-2016_05
Patent number
US09340556B2

Reaction notes

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