Hydrochloric Acid → HCID 59436192, compound

HRID 1895145Notes

Reaction equation

HRID 1895145 reaction equation
[CH3:1][O:2][C:3]1[C:4](=[O:23])[C:5]([C:19]([O:21]C)=[O:20])=[N:6][N:7]([C:9]2[CH:10]=[CH:11][CH:12]=[C:13]3[C:18]=2[N:17]=[CH:16][CH:15]=[CH:14]3)[CH:8]=1.[OH-].[Na+].C1COCC1.Cl>CO>[CH3:1][O:2][C:3]1[C:4](=[O:23])[C:5]([C:19]([OH:21])=[O:20])=[N:6][N:7]([C:9]2[CH:10]=[CH:11][CH:12]=[C:13]3[C:18]=2[N:17]=[CH:16][CH:15]=[CH:14]3)[CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 59436244HCID 59436244, compound

Product 1

HCID 59436192HCID 59436192, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of methyl 5-methoxy-4-oxo-1-quinolin-8-yl-1,4-dihydropyridazine-3-carboxylate (5.00 g, 16.1 mmol) in MeOH (64 mL) were added 1 M NaOH aqueous solution (64 mL) and THF (64 mL) at 0° C. The mixture was heated to 80° C. The homogeneous mixture was cooled to 0° C. To the mixture was added 1 M HCl aqueous solution (64 mL) at 0° C. The mixture was stirred at room temperature for 1 h and concentrated in vacuo. The precipitates were collected by filtration, washed with water and dried in vacuo at 60° C. to yield the title compound (3.59 g, 75% yield) as a fresh-colored solid: 1H NMR (DMSO-d6, 300 MHz): δ ppm 3.86 (3H, s), 7.73 (1H, dd, J=8.4, 4.3 Hz), 7.81-7.89 (1H, m), 8.12 (1H, dd, J=7.4, 1.4 Hz), 8.30 (1H, dd, J=8.4, 1.2 Hz), 8.61 (1H, dd, J=8.5, 1.6 Hz), 8.96-9.05 (2H, m).

Workup

  1. temperatureThe homogeneous mixture was cooled to 0° C
  2. concentrationconcentrated in vacuo
  3. filtrationThe precipitates were collected by filtration
  4. washwashed with water
  5. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-fc81b68fee3c4da294451bef064e33a3
Source dataset
uspto-grants-2013_08
Patent number
US08513251B2

Reaction notes

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