Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Glycolic Acid | HCID 757 | — |
| Reactant | Ammonium Hydroxide | HCID 14923 | — |
| Reactant | HCID 15224414 | HCID 15224414 | — |
| Solvent | Hydrochloric Acid | HCID 313 | — |
| Product | HCID 15224415 | HCID 15224415 | 82% |
Reaction Steps
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: 74.4; H, 5.1; N, 14.4.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06608201B2 |
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| Source dataset | uspto-grants-2003_08 |
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| ORD ID | ord-25558e2ecb9e4347ae92df79d0dd22f5 |
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| Source note | uspto-grants-2003_08 |
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