Ethoxyacetic acid → HCID 22672671, compound

HRID 991925Notes

Reaction equation

HRID 991925 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH2:18]([O:20][CH2:21][C:22](O)=O)[CH3:19].[OH-].[Na+]>O>[CH2:18]([O:20][CH2:21][C:22]1[N:12]([CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])[C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[CH:3][C:2]=2[N:1]=1)[CH3:19]

Participants

5

Reactant 3

HCID 12301Ethoxyacetic acidHCID 14798Sodium HydroxideHCID 22672668HCID 22672668, compound

Product 1

HCID 22672671HCID 22672671, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
155 °C

Procedure

3-Amino-4-(3-methylbutylamino)quinoline (7 g, 0.03 mole; Example 106) was combined with ethoxyacetic acid (8 mL, 0.08 mole) and heated at 150-160° C. for about 2 hours. The reaction mixture was cooled to room temperature, diluted with water (100 mL), made basic with sodium hydroxide and then extracted with ethyl acetate. The extract was dried over magnesium sulfate then evaporated to provide the crude product as a crystalline solid. The solid was recrystallized from hexane to provide the desired product as a solid, m.p. 64-65° C. Analysis: Calculated: %C, 72.7; %H, 7.8; %N, 14.1; Found: %C, 72.5; %H, 7.7; %N, 14.1.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried over magnesium sulfate
  4. customthen evaporated
  5. customto provide the crude product as a crystalline solid
  6. customThe solid was recrystallized from hexane

Sources & evidence

ORD record
ord-becb07fe14614c2583d34a4b3a2b7b5f
Source dataset
uspto-grants-2002_10
Patent number
US06465654B2

Reaction notes

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