Glycolic Acid → HCID 15224415, compound

HRID 2119863Notes

Reaction equation

HRID 2119863 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:20](O)(=O)[CH2:21][OH:22].[OH-].[NH4+]>Cl>[C:14]1([CH2:13][N:12]2[C:11]3[C:10]4[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=4[N:4]=[CH:3][C:2]=3[N:1]=[C:20]2[CH2:21][OH:22])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 757Glycolic AcidHCID 14923Ammonium HydroxideHCID 15224414HCID 15224414, compound

Product 1

HCID 15224415HCID 15224415, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
150 °C

Procedure

3-amino-4-(benzylamino) quinoline (9.5 g; 0.038 mol) and glycolic acid (6.8 g; 0.089 mol) were mixed and the mixture was heated at 150° C. for about 4 hr. The dark mixture was then dissolved in dilute hydrochloric acid with heating. Upon cooling a precipitate formed and was filtered from the mixture. The solid was dissolved in hot water. The solution was then made basic with ammonium hydroxide to precipitate the product. A second, less pure, small crop was obtained from the original filtrate by making it basic with ammonium hydroxide. The solid was triturated in ethyl acetate to give a green colored powder. Total yield was 82%. The product was recrystallized from methanol to give a pure sample m.p. 211-213° C. Analysis: Calculated: C, 74.7; H, 5.2; N, 14.5. Found: C, 74.4; H, 5.1; N, 14.4.

Workup

  1. temperaturewith heating
  2. temperatureUpon cooling
  3. customa precipitate formed
  4. filtrationwas filtered from the mixture
  5. dissolutionThe solid was dissolved in hot water
  6. customto precipitate the product
  7. customA second, less pure, small crop was obtained from the original filtrate
  8. customThe solid was triturated in ethyl acetate
  9. customto give a green colored powder
  10. customThe product was recrystallized from methanol
  11. customto give a pure sample m.p. 211-213° C

Sources & evidence

ORD record
ord-831950f234f542f4b218bf194a21b7bf
Source dataset
uspto-grants-2004_02
Patent number
US06686472B2

Reaction notes

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