Sodium Hydroxide → HCID 11163718, compound

HRID 1822829Notes

Reaction equation

HRID 1822829 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[N:15]=[CH:14][C:13]([C:21]([O:23]CC)=[O:22])=[C:12]2[Cl:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>O1CCCC1.CO>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[N:15]=[CH:14][C:13]([C:21]([OH:23])=[O:22])=[C:12]2[Cl:26])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22170246HCID 22170246, compound

Product 1

HCID 11163718HCID 11163718, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 6-(Benzyloxy)-4-chloro-7-methoxy-3-quinolinecarboxylate (11.9 g, 32 mmol) was dissolved in a mixture of tetrahydrofurane (THF) and methanol (300 ml) in a ratio of 1:1. Aqueous sodium hydroxide (2.0 M, 65 ml, 130 mmol) was added and the mixture stirred at room temperature for 2 hours. The organic solvents were removed by rotatory evaporation and the resulting solution diluted with more water (200 ml) cooled on ice and acidified to pH 2–3 with hydrochloric acid under vigorous stirring. The precipitate was filtered off washed twice with water, twice with ethanol and ether and finally dried in vacuum at 50° C. over night to give a white solid, 11.0 g (100% yield).

Workup

  1. customThe organic solvents were removed by rotatory evaporation
  2. additionthe resulting solution diluted with more water (200 ml)
  3. temperaturecooled on ice
  4. filtrationThe precipitate was filtered off
  5. washwashed twice with water, twice with ethanol and ether
  6. customfinally dried in vacuum at 50° C. over night
  7. customto give a white solid, 11.0 g (100% yield)

Sources & evidence

ORD record
ord-a4a7d81a95214d43b79b079642b0292e
Source dataset
uspto-grants-2006_05
Patent number
US07037925B2

Reaction notes

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