Hydrochloric Acid → HCID 86732836, compound

HRID 525971Notes

Reaction equation

HRID 525971 reaction equation
N[C:2]1[C:11]([O:12]C)=[C:10]([O:14][CH3:15])[CH:9]=[C:8]2[C:3]=1[C:4](=[O:22])[C:5]([C:19]([OH:21])=[O:20])=[CH:6][N:7]2[CH:16]1[CH2:18][CH2:17]1.[ClH:23].N([O-])=O.[Na+]>O>[Cl:23][C:2]1[C:11]([OH:12])=[C:10]([O:14][CH3:15])[CH:9]=[C:8]2[C:3]=1[C:4](=[O:22])[C:5]([C:19]([OH:21])=[O:20])=[CH:6][N:7]2[CH:16]1[CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 23668193Sodium NitriteHCID 86732835HCID 86732835, compound

Product 1

HCID 86732836HCID 86732836, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
95 °C

Procedure

To a pale brown suspension of 5-amino-1-cyclopropyl-6,7-dimethoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (9 g, 29.6 mmol) in con. HCl (60 mL) stirred at 0° C. was added dropwise a cold solution of sodium nitrite (2.143 g, 31.1 mmol) in Water (20.00 mL). Stirring continued at 0° C. for 1 h. LCMS indicated completion of reaction. HCl (80 mL, 2633 mmol) was added and the mixture was heated at 95° C. for 6 h. LCMS indicated completion of reaction. The reaction mixture was cooled down to rt and then poured into water. The precipitates were collected by filtration and dried to afford 5-chloro-1-cyclopropyl-6-hydroxy-7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (7.4 g, 23.89 mmol, 81% yield) as a pale yellow solid. LCMS: [M+H]+: 310.1.

Workup

  1. customcompletion of reaction
  2. customcompletion of reaction
  3. temperatureThe reaction mixture was cooled down to rt
  4. filtrationThe precipitates were collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-18b67dbacc4145b3bcf194551bd7cce2
Source dataset
uspto-grants-2016_05
Patent number
US09340556B2

Reaction notes

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