Hydrochloric Acid → 7-bromo-4-hydroxy-1-(propan-2-yl)quinolin-2(1H)-one

HRID 1754559Notes

Reaction equation

HRID 1754559 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:21])[CH:7](C(OCC)=O)[C:8](=[O:15])[N:9]2[CH:12]([CH3:14])[CH3:13])=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CN1C(=O)CCC1>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:21])=[CH:7][C:8](=[O:15])[N:9]2[CH:12]([CH3:13])[CH3:14])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86679803Ethyl 7-bromo-2,4-dioxo-1-(propan-2-yl)-1,2,3,4-tetrahydroquinoline-3-carboxylate

Product 1

HCID 866798047-bromo-4-hydroxy-1-(propan-2-yl)quinolin-2(1H)-oneYield 91%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A suspension of ethyl 7-bromo-2,4-dioxo-1-(propan-2-yl)-1,2,3,4-tetrahydroquinoline-3-carboxylate (1.5 g, 4.23 mmol) in sodium hydroxide (2M solution, 32 mL, 64 mmol) is heated to reflux. The reaction medium becomes homogeneous and, after 3 hours, a suspension is once again observed. 6 mL of NMP are added to homogenize, and the resulting mixture is than refluxed for 12 hours. The solution cooled to room temperature is poured into 6M hydrochloric acid solution to give a white precipitate, which is filtered off. After rinsing with water and drying the precipitate under vacuum, 1.1 g of a white solid are obtained (yield: 91%).

Workup

  1. temperatureis heated to reflux
  2. temperaturethan refluxed for 12 hours
  3. customto give a white precipitate, which
  4. filtrationis filtered off
  5. washAfter rinsing with water
  6. dry with materialdrying the precipitate under vacuum, 1.1 g of a white solid
  7. customare obtained (yield: 91%)

Sources & evidence

ORD record
ord-04190063de69446aba03eb70a7df73d6
Source dataset
uspto-grants-2015_10
Patent number
US09169246B2

Reaction notes

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