HCID 178423389, compound → 6-Methylquinolin-3-amine

HRID 430549Notes

Reaction equation

HRID 430549 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([N+:12]([O-])=O)=[C:5]2O>[Pt].C(O)C.[OH-].[NH4+]>[NH2:12][C:6]1[CH:7]=[N:8][C:9]2[C:4]([CH:5]=1)=[CH:3][C:2]([CH3:1])=[CH:11][CH:10]=2

Participants

5

Reactant 1

HCID 178423389HCID 178423389, compound

Product 1

HCID 221488796-Methylquinolin-3-amineYield 64.5%

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 702EthanolSolventHCID 14923Ammonium HydroxideSolvent

Procedure

Catalyst (0.10 g of 10% platinum on carbon) was added to a solution of 6-methyl-3-nitroquinolin-4-ol (1 g) in ethanol (25 mL) and ammonium hydroxide (0.5 mL). The mixture was reduced on a Parr apparatus at ambient temperature under a hydrogen atmosphere. The reaction mixture was filtered to remove the catalyst and then concentrated under vacuum. The residue was combined with water and heated. Hydrochloric acid was added dropwise until all of the solid had dissolved. Activated carbon was added to the solution. The mixture was filtered. Hydrochloric acid (2 mL of 12N) was added to the filtrate. This recrystallization was run three times to provide 0.50 g of 3-amino-6-methylquinolin-+4ol hydrochloride, m.p. >310° C. Analysis: Calculated for C10H10N2O.HCl: % C, 57.02; % H, 5.26; % N, 13.30; Found: % C, 56.92; % H, 5.16; % N, 13.24.

Workup

  1. customwas reduced on a Parr apparatus at ambient temperature under a hydrogen atmosphere
  2. filtrationThe reaction mixture was filtered
  3. customto remove the catalyst
  4. concentrationconcentrated under vacuum
  5. temperatureheated
  6. additionHydrochloric acid was added dropwise until all of the solid
  7. dissolutionhad dissolved
  8. additionActivated carbon was added to the solution
  9. filtrationThe mixture was filtered
  10. additionHydrochloric acid (2 mL of 12N) was added to the filtrate
  11. customThis recrystallization

Sources & evidence

ORD record
ord-dd1ae662cb8d46e7813abd06ae707f50
Source dataset
uspto-grants-2001_11
Patent number
US06323200B1

Reaction notes

Loading…