Sodium Hydroxide → 4-(2-Amino-ethoxy)-[1,10]phenanthroline-2-carbaldehyde oxime

HRID 2046527Notes

Reaction equation

HRID 2046527 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][O:10][C:11]1[C:24]2[C:15](=[C:16]3[C:21](=[CH:22][CH:23]=2)[CH:20]=[CH:19][CH:18]=[N:17]3)[N:14]=[C:13]([CH:25]=O)[CH:12]=1)(C)(C)C.Cl.[NH2:29][OH:30].[OH-].[Na+]>FC(F)(F)C(O)=O.C(Cl)Cl.O>[NH2:7][CH2:8][CH2:9][O:10][C:11]1[C:24]2[C:15](=[C:16]3[C:21](=[CH:22][CH:23]=2)[CH:20]=[CH:19][CH:18]=[N:17]3)[N:14]=[C:13]([CH:25]=[N:29][OH:30])[CH:12]=1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 59497137HCID 59497137, compound

Product 1

HCID 1363463964-(2-Amino-ethoxy)-[1,10]phenanthroline-2-carbaldehyde oxime

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of [2-(2-formyl-[1,10]phenanthrolin-4-yloxy)-ethyl]carbamic acid tert-butyl ester (0.52 g, 1.4 mmol) was stirred for 1 hour at room temperature in a mixture of trifluoroacetic acid (5 mL) and methylene chloride (10 mL). The solvent was removed and the residue was dried and redissolved in ethanol (5 mL). A solution of hydroxylamine hydrochloride (0.88 g, 12.7 mmol) in water (7 mL) was added followed by the addition of 10% NaOH until a white precipitate formed. The mixture was heated to reflux for 1 hour, cooled down to room temperature and the white precipitate filtered, washed with cold water and dried. The title compound was isolated as a pale solid (37.0 mg, 9%)

Workup

  1. customThe solvent was removed
  2. customthe residue was dried
  3. dissolutionredissolved in ethanol (5 mL)
  4. customformed
  5. temperatureThe mixture was heated
  6. temperatureto reflux for 1 hour
  7. filtrationthe white precipitate filtered
  8. washwashed with cold water
  9. customdried

Sources & evidence

ORD record
ord-a76182a080054f9382fa063cc3e2488d
Source dataset
uspto-grants-2013_11
Patent number
US08592446B2

Reaction notes

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