Sodium Hydroxide → HCID 22643234, compound

HRID 2414755Notes

Reaction equation

HRID 2414755 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([NH:12]C(=O)C)[CH:10]=2)[N:5]=[C:4]([C:16]2[CH:21]=[CH:20][C:19]([CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)=[CH:18][CH:17]=2)[CH:3]=1.[OH-].[Na+]>Cl>[CH:22]1([C:19]2[CH:18]=[CH:17][C:16]([C:4]3[CH:3]=[C:2]([NH2:1])[C:11]4[C:6](=[CH:7][CH:8]=[C:9]([NH2:12])[CH:10]=4)[N:5]=3)=[CH:21][CH:20]=2)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22643183HCID 22643183, compound

Product 1

HCID 22643234HCID 22643234, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
95 °C

Procedure

N-[4-Amino-2-(4-cyclohexylphenyl)-quinolin-6-yl]-acetamide (22 g) was placed in a 1 L flask to which 500 mL of 6 N HCl was added and the mixture heated with stirring to 95° C. for 18 hrs. After this time, the solution was cooled in ice and was then cautiously neutralized with concentrated NaOH solution, followed by adjustment to pH 9.5. The solution was then poured into a 2 L separatory funnel and extracted with ethyl acetate. The organic layer was then dried over Na2SO4, filtered and concentrated to give 17 g of the desired product. Repeated crystallization using methanol, methylene chloride and hexane provided 9.0 g (41%) of the pure title compound.

Workup

  1. additionwas added
  2. temperaturethe mixture heated
  3. temperatureAfter this time, the solution was cooled in ice
  4. additionThe solution was then poured into a 2 L separatory funnel
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic layer was then dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-46a1bce4257349b38391b9a69d214e9d
Source dataset
uspto-grants-2004_11
Patent number
US06815447B2

Reaction notes

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