Water → HCID 15463314, compound

HRID 1596386Notes

Reaction equation

HRID 1596386 reaction equation
[CH:1](=[N:19][OH:20])[C:2]1[CH2:3][O:4][C:5]2[CH:11]=[CH:10][C:9]([CH2:12][C:13]3[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=3)=[CH:8][C:6]=2[CH:7]=1.O.N.O.[OH-].[Na+]>C(Cl)Cl.FC(F)(F)C(O)=O>[N:15]1[CH:16]=[CH:17][CH:18]=[C:13]([CH2:12][C:9]2[CH:10]=[CH:11][C:5]3[O:4][CH2:3][C:2]([CH2:1][NH:19][OH:20])=[CH:7][C:6]=3[CH:8]=2)[CH:14]=1

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 12896473Azane;hydrateHCID 73198224HCID 73198224, compound

Product 1

HCID 15463314HCID 15463314, compoundYield 86.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

13.1 ml of borane-pyridine complex was added dropwise to a mixture of 3.46 g (13.0 mmol) of 3-formyl-6-(3-pyridylmethyl)-2H-1-benzopyran oxime in methylene chloride (16 ml) and trifluoroacetic acid (16 ml) at −23° C. over 10 minutes and the mixture was stirred at the same temperature for 30 minutes, followed by addition of concentrated ammonia water to neutralize the acid. Then, water and an aqueous 10% sodium hydroxide solution were added to make the mixture basic, followed by extraction with ethyl acetate. After the organic layer was washed with water and brine, the solvent was evaporated in vacuo. The residue was purified by Florisil (Trademark) column chromatography (chloroform: methanol=50:1-15:1) to obtain 3.03 g (yield=86.9%) of the desired compound as an oil.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washAfter the organic layer was washed with water and brine
  3. customthe solvent was evaporated in vacuo
  4. customThe residue was purified by Florisil (Trademark) column chromatography (chloroform: methanol=50:1-15:1)

Sources & evidence

ORD record
ord-c6407420963f4edeb5de3ce26963bf9e
Source dataset
uspto-grants-2001_09
Patent number
US06291482B1

Reaction notes

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