Sodium Acetate → HCID 66713166, compound

HRID 1618300Notes

Reaction equation

HRID 1618300 reaction equation
[CH2:1]([O:5][C:6]([C:8]1[N:9]=[C:10](Cl)[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][C:14]([O:19][C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-])=O)=[CH:22][CH:21]=1)=[CH:13][CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4].C([O-])(=O)C.[Na+]>C1COCC1.CO.[Pd]>[CH2:1]([O:5][C:6]([C:8]1[N:9]=[CH:10][C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][C:14]([O:19][C:20]1[CH:21]=[CH:22][C:23]([NH2:26])=[CH:24][CH:25]=1)=[CH:13][CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 2

HCID 517045Sodium AcetateHCID 86595480HCID 86595480, compound

Product 1

HCID 66713166HCID 66713166, compoundYield 69.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

100 mg of 1-chloro-4-hydroxy-6-(4-nitro-phenoxy)-isoquinoline-3-carboxylic acid butyl ester was dissolved in 3 ml THF and 3 ml methanol. 20 mg of sodium acetate and 25 mg of 10% palladium on carbon were added to the mixture, and the stirring reaction was placed under hydrogen atmosphere (balloon) overnight. The resultant solution was filtered through a pad of celite and concentrated to a residue. The crude material was purified by column chromatography on silica gel, eluting the product with a gradient of 0-20% ethyl acetate in dichloromethane, to produce 59 mg of product; MS (−): m/z 351.27 (M−1).

Workup

  1. customthe stirring reaction
  2. custom(balloon) overnight
  3. filtrationThe resultant solution was filtered through a pad of celite
  4. concentrationconcentrated to a residue
  5. customThe crude material was purified by column chromatography on silica gel
  6. washeluting the product with a gradient of 0-20% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-e3595d3a3fb14bd2acd843f477d18d3f
Source dataset
uspto-grants-2014_07
Patent number
US08765956B2

Reaction notes

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