Sodium Hydroxide → HCID 178496654, compound

HRID 1486931Notes

Reaction equation

HRID 1486931 reaction equation
[OH-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][C:8]([C:14]([O:16]CC)=[O:15])=[C:7]2[NH:19][C@H:20]1[CH2:23][C@@H:22]([O:24][CH3:25])[CH2:21]1>CO.C1COCC1>[Br:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][C:8]([C:14]([OH:16])=[O:15])=[C:7]2[NH:19][C@H:20]1[CH2:23][C@@H:22]([O:24][CH3:25])[CH2:21]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 178469500HCID 178469500, compound

Product 1

HCID 178496654HCID 178496654, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Sodium hydroxide (190 ml, 379.70 mmol) was added to ethyl 6-bromo-4-[(cis-3-methoxycyclobutyl)amino]quinoline-3-carboxylate (36 g, 94.92 mmol) in a mixture of MeOH (120 mL) and THF (120 mL) and the resulting mixture stirred at 60° C. for 3 h. The solvent was removed under reduced pressure and the mixture adjusted to pH 3 with 2M hydrochloric acid. The precipitate was collected by filtration, washed with water (300 mL) and dried under vacuum to afford the desired material (33.0 g, 99%) as a pale yellow solid, which was used without further purification. Mass Spectrum: m/z (ES+)[M+H]+=351.

Workup

  1. customThe solvent was removed under reduced pressure
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water (300 mL)
  4. customdried under vacuum

Sources & evidence

ORD record
ord-1ec2c50a2970448aaf4c1657b8981318
Source dataset
uspto-grants-2016_08
Patent number
US09428503B2

Reaction notes

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