Hydrochloric Acid → Ethyl 5-chloro-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate

HRID 889610Notes

Reaction equation

HRID 889610 reaction equation
[H-].[Na+].[C:3]([O:11][CH2:12][CH3:13])(=[O:10])[CH2:4][C:5]([O:7]CC)=O.O.Cl.[Cl:16][C:17]1[C:26]2[C:25](=O)[O:24][C:23](=O)[N:22](C)[C:21]=2[CH:20]=[CH:19][CH:18]=1>>[Cl:16][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]2[C:26]=1[C:25]([OH:24])=[C:4]([C:3]([O:11][CH2:12][CH3:13])=[O:10])[C:5](=[O:7])[N:22]2[CH3:23]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 5867555-Chloro-1-methyl-1H-benzo[d][1,3]oxazine-2,4-dione2×

Product 1

HCID 54717770Ethyl 5-chloro-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylateYield 18%

Conditions

Temperature
85 °C

Procedure

Sodium hydride (1.9 g, 79.17 mmol, 1.60 equiv) was added in several portions to the mixture of 5-chloro-1-methyl-1H-benzo[d][1,3]oxazine-2,4-dione in N,N-dimethylformamide from Step 2. Diethyl malonate (7.7 g, 48.07 mmol, 1.00 equiv) was then added dropwise to the stirred mixture over a period of about 30 minutes. The resulting solution was stirred at about 85° C. for about 1 hour, water (800 ml) was added, and the pH of the solution was adjusted to 2 with a solution of hydrochloric acid (5 mol/L). The resulting crude product was collected by filtration and then re-crystallized in ethanol to give the title product as a light yellow solid (2.5 g, yield: 18% 2 steps).

Workup

  1. filtrationThe resulting crude product was collected by filtration
  2. customre-crystallized in ethanol

Sources & evidence

ORD record
ord-905d114bff0b467d914523935483f670
Source dataset
uspto-grants-2012_08
Patent number
US08252933B2

Reaction notes

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