Hydrochloric Acid → 4-(4-Fluoro-benzylamino)-2-hydroxy-benzonitrile

HRID 18461Notes

Reaction equation

HRID 18461 reaction equation
[F:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][NH:7][C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10]([O:16]COCCOC)[CH:9]=2)=[CH:4][CH:3]=1.Cl>C1COCC1>[F:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][NH:7][C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10]([OH:16])[CH:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68585671HCID 68585671, compound

Product 1

HCID 103994684-(4-Fluoro-benzylamino)-2-hydroxy-benzonitrileYield 20.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(4-fluoro-benzylamino)-2-(2-methoxy-ethoxymethoxy)-benzonitrile (15 mg; 0.05 mmol) in THF (1 mL) was added 4 M HCl (aq.; 0.5 mL). The mixture was refluxed for 2 h, cooled and the precipitate filtered off. Purification by flash column chromatography (SiO2—MeOH/CH2Cl2=0:1 to 5:95) yielded 2.5 mg pure product.

Workup

  1. temperatureThe mixture was refluxed for 2 h
  2. temperaturecooled
  3. filtrationthe precipitate filtered off
  4. customPurification by flash column chromatography (SiO2—MeOH/CH2Cl2=0:1 to 5:95)

Sources & evidence

ORD record
ord-9f9b3dff3ba042cf8e9a4d1b7eb1e0cc
Source dataset
uspto-grants-2010_06
Patent number
US07741352B2

Reaction notes

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