Hydrochloric Acid → HCID 20570075, compound

HRID 1577852Notes

Reaction equation

HRID 1577852 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:14]([OH:16])=[O:15].[OH-].[Na+].[CH2:19](Br)[CH2:20][CH2:21][CH3:22].Cl>O.CS(C)=O>[CH2:19]([N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[CH:7]=2)[C:2](=[O:1])[C:3]([C:14]([OH:16])=[O:15])=[CH:4]1)[CH2:20][CH2:21][CH3:22]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8002Butyl bromideHCID 14798Sodium HydroxideHCID 178487721HCID 178487721, compound

Product 1

HCID 20570075HCID 20570075, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

11.0 g. (50 millimoles) of 4-hydroxy-7-methoxyquinoline-3-carboxylic acid is introduced into a suspension of 14.0 g. (351 millimoles) of pulverized sodium hydroxide in 200 ml. of dimethyl sulfoxide. The mixture is stirred for 10 minutes at room temperature, and then 16.1 ml. (150 mmol) of butyl bromide is added dropwise thereto so that the temperature does not exceed 25° C. Thereafter, the mixture is stirred for 2 hours at room temperature, poured into water, and acidified with hydrochloric acid. The thus-precipitated product is filtered off, washed with water, dried, and recrystallized from dimethylformamide.

Workup

  1. customdoes not exceed 25° C
  2. stirringThereafter, the mixture is stirred for 2 hours at room temperature
  3. filtrationThe thus-precipitated product is filtered off
  4. washwashed with water
  5. customdried
  6. customrecrystallized from dimethylformamide

Sources & evidence

ORD record
ord-77f029e0e83744bb88610b960aa622b0
Source dataset
uspto-grants-1981_09
Patent number
US04289777

Reaction notes

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