Hydrochloric Acid → HCID 86732791, compound

HRID 525924Notes

Reaction equation

HRID 525924 reaction equation
[NH2:1][C:2]1[C:11]2[O:12][CH2:13][O:14][C:10]=2[CH:9]=[C:8]2[C:3]=1[C:4](=[O:20])[C:5]([C:17]([OH:19])=[O:18])=[N:6][N:7]2[CH2:15][CH3:16].[N:21]([O-])=O.[Na+].[ClH:25]>O>[Cl-:25].[C:17]([C:5]1[C:4](=[O:20])[C:3]2[C:2]([N+:1]#[N:21])=[C:11]3[O:12][CH2:13][O:14][C:10]3=[CH:9][C:8]=2[N:7]([CH2:15][CH3:16])[N:6]=1)([OH:19])=[O:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23668193Sodium NitriteHCID 86732790HCID 86732790, compound

Product 1

HCID 86732791HCID 86732791, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 5-amino-1-ethyl-4-oxo-1,4-dihydro-[1,3]dioxolo[4,5-g]cinnoline-3-carboxylic acid (3.6 g, 12.99 mmol) in hydrochloric acid (conc) (20 ml) was stirred at room temperature and sodium nitrite (0.986 g, 14.28 mmol) in water (7 mL) was added dropwise to maintain the temperature bellow 45° C. Stirring continued for 5 h. The solution was poured into 50 ml of water and was allowed to stand overnight in the refrigerator. Precipitate was collected by filtration and dried over drierite in a desiccator to yield 3-Carboxy-1-ethyl-4-oxo-1,4-dihydro-[1,3]dioxolo[4,5-g]cinnoline-5-diazonium chloride (3.15 g, 9.67 mmol, 74.5% yield). LCMS: (M+H)+: 326.2

Workup

  1. temperatureto maintain the temperature bellow 45° C
  2. stirringStirring
  3. waitto stand overnight in the refrigerator
  4. filtrationPrecipitate was collected by filtration
  5. dry with materialdried over drierite in a desiccator

Sources & evidence

ORD record
ord-7a91a269a61c4acea9f412832ec75af3
Source dataset
uspto-grants-2016_05
Patent number
US09340556B2

Reaction notes

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