Ammonium formate → 1-Cyano-4,7-dihydroxy-isoquinoline-3-carboxylic acid ethyl ester

HRID 409332Notes

Reaction equation

HRID 409332 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([C:25]#[N:26])[C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][CH:12]=[C:11]([O:17]CC1C=CC=CC=1)[CH:10]=2)=[O:5])[CH3:2].C([O-])=O.[NH4+]>CCOC(C)=O.CCO.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([C:25]#[N:26])[C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][CH:12]=[C:11]([OH:17])[CH:10]=2)=[O:5])[CH3:2]

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 671102297-Benzyloxy-1-cyano-4-hydroxy-isoquinoline-3-carboxylic acid ethyl ester

Product 1

HCID 671102341-Cyano-4,7-dihydroxy-isoquinoline-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-Cyano-4,7-dihydroxy-isoquinoline-3-carboxylic acid ethyl ester was prepared by heating a mixture of 175 mg (0.50 mmol) of 7-Benzyloxy-1-cyano-4-hydroxy-isoquinoline-3-carboxylic acid ethyl ester (example 52h), 630 mg (10 mmol) of ammonium formate, and 40 mg of 10% Pd/C in 3 mL of 1:1 EtOAc and EtOH at reflux temperature for 40 min. The resultant mixture was cooled, filtered through a celite pad to remove solids, and concentrated to a crude solid. The solid was triturated with hot ethanol to give 56 mg of off-white solid upon drying; MS (ESI+): 259.3 e/z (M+1)

Workup

  1. temperatureby heating
  2. temperatureat reflux temperature for 40 min
  3. filtrationfiltered through a celite pad
  4. customto remove solids
  5. concentrationconcentrated to a crude solid
  6. customThe solid was triturated with hot ethanol

Sources & evidence

ORD record
ord-78957fe569a24565a51e01b7326f8b9c
Source dataset
uspto-grants-2014_06
Patent number
US08759373B2

Reaction notes

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