Hydrochloric Acid → HCID 70496900, compound

HRID 2408126Notes

Reaction equation

HRID 2408126 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:18][C:17]([CH3:20])([CH3:19])[C:16]3[C:11](=[CH:12][N:13]=C(C#N)[CH:15]=3)[NH:10]2)[CH:5]=[CH:6][C:7]=1[F:8].[OH-:23].[Na+].Cl.[CH2:26]([OH:28])[CH3:27]>O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:18][C:17]([CH3:20])([CH3:19])[C:16]3[C:11](=[CH:12][N:13]=[C:27]([C:26]([OH:23])=[O:28])[CH:15]=3)[NH:10]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 70496562HCID 70496562, compound

Product 1

HCID 70496900HCID 70496900, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred mixture solution of 2-(3-chloro-4-fluoro-phenyl)-4,4-dimethyl-1,2,3,4-tetrahydro-[1,7]naphthyridine-6-carbonitrile (315.0 mg, 1.0 mmol) in ethanol (10.0 mL) was added 50% sodium hydroxide in water (3.5 mL). The reaction mixture was stirred at 90° C. for 6 h. The mixture was neutralized with a 3 N aqueous hydrochloric acid solution and extracted with ethyl acetate (2×100 mL), washed with water, dried over anhydrous sodium sulfate and then concentrated in vacuo to afford 2-(3-chloro-4-fluoro-phenyl)-4,4-dimethyl-1,2,3,4-tetrahydro-[1,7]naphthyridine-6-carboxylic acid (317.9 mg, 95%) as a light white solid which was used for next step without further purification: MS (ESI) M+1=335.1.

Workup

  1. extractionextracted with ethyl acetate (2×100 mL)
  2. washwashed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-618588d08a82435084286e7eaa1960d7
Source dataset
uspto-grants-2014_08
Patent number
US08809369B2

Reaction notes

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