Hydrochloric Acid → HCID 54588554, compound

HRID 1467032Notes

Reaction equation

HRID 1467032 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[O:12][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[N:5]=[C:4]([CH3:19])[C:3]=1[C:20]([O:22]CC)=[O:21].[OH-].[Na+].Cl>CCO.O>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[O:12][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[N:5]=[C:4]([CH3:19])[C:3]=1[C:20]([OH:22])=[O:21]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66746528HCID 66746528, compound

Product 1

HCID 54588554HCID 54588554, compoundYield 99.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of ethyl 4-amino-5-(cyclohexyloxy)-2-methylquinoline-3-carboxylate (Example 36a, 110 g, 0.335 mol) in EtOH (450 mL) was added a solution of NaOH (33.5 g, 0.837 mol) in water (200 mL) at room temperature. The reaction mixture was then refluxed overnight. The reaction solution was cooled down to 0° C. and carefully neutralized with 4N HCl to pH 7. The resultant solution was concentrated under reduced pressure to remove most of the EtOH. The precipitate was collected by filtration, and re-dissolved in EtOH (4 L) at 65° C. and treated with activated charcoal (5 g) for 0.5 h. The charcoal was removed by filtration over celite, and the filtrate was concentrated. The precipitate was collected by filtration, washed with cold water, and dried under vacuum at 60° C. overnight to give the title compound as a white solid (100 g, 99%). M.p.: 220.0-221.5° C. 1H NMR (400 MHz, DMSO-d6) δ 1.28-1.72 (m, 8H), 2.00-2.04 (m, 2H), 2.75 (s, 3H), 4.69-4.71 (m, 1H), 7.10-7.12 (d, J=8.0 Hz, 1H), 7.24-7.26 (d, J=8.0 Hz, 1H), 7.65 (t, J=8.0 Hz, 1H), 12.80 (brs, 1H). MS 301 (MH+). Elemental Analysis Calculated (Found) for C17H20N2O3: C, 67.98%; (67.74%); H, 6.71%; (7.01%); N, 9.33%; (9.40%).

Workup

  1. temperatureThe reaction mixture was then refluxed overnight
  2. concentrationThe resultant solution was concentrated under reduced pressure
  3. customto remove most of the EtOH
  4. filtrationThe precipitate was collected by filtration
  5. dissolutionre-dissolved in EtOH (4 L) at 65° C.
  6. additiontreated with activated charcoal (5 g) for 0.5 h
  7. customThe charcoal was removed by filtration over celite
  8. concentrationthe filtrate was concentrated
  9. filtrationThe precipitate was collected by filtration
  10. washwashed with cold water
  11. customdried under vacuum at 60° C. overnight

Sources & evidence

ORD record
ord-185ebb769fcd4f049aff9c79dd305f20
Source dataset
uspto-grants-2015_04
Patent number
US09000054B2

Reaction notes

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