Hydrochloric Acid → 2-(1-Cyano-4,7-dihydroxyisoquinoline-3-carboxamido)acetic acid

HRID 409333Notes

Reaction equation

HRID 409333 reaction equation
C(O[C:4]([C:6]1[N:7]=[C:8]([C:18]#[N:19])[C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][CH:12]=[C:11]([OH:17])[CH:10]=2)=[O:5])C.[NH2:20][CH2:21][C:22]([OH:24])=[O:23].Cl.O>C[O-].[Na+].CO>[C:18]([C:8]1[C:9]2[C:14](=[CH:13][CH:12]=[C:11]([OH:17])[CH:10]=2)[C:15]([OH:16])=[C:6]([C:4]([NH:20][CH2:21][C:22]([OH:24])=[O:23])=[O:5])[N:7]=1)#[N:19]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 750GlycineHCID 962WaterHCID 671102341-Cyano-4,7-dihydroxy-isoquinoline-3-carboxylic acid ethyl ester

Product 1

HCID 247811412-(1-Cyano-4,7-dihydroxyisoquinoline-3-carboxamido)acetic acidYield 86%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 10942334Sodium MethoxideSolvent

Procedure

[(1-Cyano-4,7-dihydroxy-isoquinoline-3-carbonyl)-amino]-acetic acid was prepared by heating a mixture of 42 mg (0.162 mmol) of 1-Cyano-4,7 dihydroxy-isoquinoline-3-carboxylic acid ethyl ester and 97 mg (1.29 mmol) of glycine in 2.25 mL of 0.5 N NaOMe in methanol at reflux temperature for 26 hours. The reaction mixture was cooled and acidified with 3 mL of 1 N HCl and water. A white solid was collected on a medium glass fritted filter to provide 40 mg of the title compound; MS (ESI+): 288.2 e/z (M+1)

Workup

  1. custom[(1-Cyano-4,7-dihydroxy-isoquinoline-3-carbonyl)-amino]-acetic acid was prepared
  2. temperatureby heating
  3. temperatureat reflux temperature for 26 hours
  4. temperatureThe reaction mixture was cooled
  5. customA white solid was collected on a medium glass fritted filter

Sources & evidence

ORD record
ord-1e28793e89ce42669caaf06186509bb2
Source dataset
uspto-grants-2014_06
Patent number
US08759373B2

Reaction notes

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