Hydrochloric Acid → Chloride

HRID 525898Notes

Reaction equation

HRID 525898 reaction equation
[NH2:1][C:2]1[C:3]2[C:4](=[O:20])[C:5]([C:17]([OH:19])=[O:18])=[CH:6][N:7]([CH2:15][CH3:16])[C:8]=2[CH:9]=[C:10]2[O:14][CH2:13][O:12][C:11]=12.[ClH:21].[N:22]([O-])=O.[Na+]>O>[C:17]([C:5]1[C:4](=[O:20])[C:3]2[C:2]([N+:1]#[N:22])=[C:11]3[O:12][CH2:13][O:14][C:10]3=[CH:9][C:8]=2[N:7]([CH2:15][CH3:16])[CH:6]=1)([OH:19])=[O:18].[Cl-:21]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 30400661,3-Dioxolo(4,5-g)quinoline-7-carboxylic acid, 5,8-dihydro-9-amino-5-ethyl-8-oxo-HCID 23668193Sodium Nitrite

Product 2

HCID 312ChlorideYield 38.8%HCID 12873127HCID 12873127, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a pale brown suspension of 9-amino-5-ethyl-8-oxo-5,8-dihydro-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid (11 g, 39.8 mmol) in con. HCl (25 mL) stirred at r.t. was added dropwise sodium nitrite (3.57 g, 51.8 mmol) in water (9 mL) at such a rate that the temperature of the reaction mixture would not exceed 45° C. (Ice bath!Slow addition!). Stirring continued for 5 h. The solution was poured into 120 mL of water and allowed to stand overnight in the refrigerator. The precipitate was collected by filtration, washed with water and dried to afford 7-carboxy-5-ethyl-8-oxo-5,8-dihydro-[1,3]dioxolo[4,5-g]quinoline-9-diazonium, Chloride (5 g, 15.45 mmol, 38.8% yield). LCMS: (M+H)+: 324.2.

Workup

  1. customexceed 45° C.
  2. addition(Ice bath!Slow addition!)
  3. waitto stand overnight in the refrigerator
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-fd1418d74ae44cd88fb7484d350dc4ec
Source dataset
uspto-grants-2016_05
Patent number
US09340556B2

Reaction notes

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