Hydrochloric Acid → HCID 178432179, compound

HRID 2410189Notes

Reaction equation

HRID 2410189 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[O:12][CH2:13][C:14]([NH2:17])([CH3:16])[CH3:15])[N:5]=[C:4]([CH3:18])[C:3]=1[C:19]([O:21]CC)=[O:20].[OH-].[Na+].[ClH:26]>CCO.O>[Cl-:26].[NH3+:17][C:14]([CH3:16])([CH3:15])[CH2:13][O:12][C:10]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:11]=1[C:2]([NH3+:1])=[C:3]([C:19]([OH:21])=[O:20])[C:4]([CH3:18])=[N:5]2.[Cl-:26]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66746535HCID 66746535, compound

Product 1

HCID 178432179HCID 178432179, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of ethyl 4-amino-5-(2-amino-2-methylpropoxy)-2-methylquinoline-3-carboxylate (Example Db) (0.65 g, 2.05 mmol) in EtOH (35 mL) was added a solution of NaOH in H2O (2.0 M, 5.2 mL) at room temperature under a nitrogen atmosphere. The obtained reaction mixture was heated at 80° C. over 3 h and cooled to room temperature. The pH of the cold mixture was adjusted to 1 with a solution of HCl (1.5 M) and the acidified solution was evaporated to dryness. The residue was dissolved in a mixture of EtOH and H2O (30 mL, 1:1) and the product was isolated by preparative HPLC (RPC18, H2O→CH3CN gradient). The appropriate fractions were collected and evaporated under reduced pressure. The residue was dried in a dessicator over phosphorus pentoxide to give 0.41 g (54%) 5-(2-ammonio-2-methylpropoxy)-3-carboxy-2-methylquinolin-4-aminium chloride as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 10.05-9.90 (m, 1H), 9.15-9.00 (m, 1H), 8.69-8.57 (m, 3H), 7.91 (t, J=8.3 Hz, 1H), 7.65 (d, J=8.0 Hz, 1H), 7.38 (d, J=8.3 Hz, 1H), 4.39 (s, 2H), 2.84 (s, 3H), 1.44 (s, 6H). MS 291 (M+)

Workup

  1. customat room temperature
  2. customThe obtained reaction mixture
  3. temperaturecooled to room temperature
  4. customthe acidified solution was evaporated to dryness
  5. dissolutionThe residue was dissolved in a mixture of EtOH and H2O (30 mL, 1:1)
  6. customthe product was isolated by preparative HPLC (RPC18, H2O→CH3CN gradient)
  7. customThe appropriate fractions were collected
  8. customevaporated under reduced pressure
  9. dry with materialThe residue was dried in a dessicator over phosphorus pentoxide

Sources & evidence

ORD record
ord-2d5b415dda234c8a81fda9cbebd08469
Source dataset
uspto-grants-2014_08
Patent number
US08815956B2

Reaction notes

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