Hydrochloric Acid → HCID 89812857, compound

HRID 1481024Notes

Reaction equation

HRID 1481024 reaction equation
[C:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:11]=2)[C:6]([OH:20])=[C:5]([C:21]([O:23]C)=[O:22])[N:4]=1)#[N:2].[OH-].[Na+].C1COCC1.Cl>O.CCOC(C)=O.CO>[C:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:11]=2)[C:6]([OH:20])=[C:5]([C:21]([OH:23])=[O:22])[N:4]=1)#[N:2]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 89812860Methyl 1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxylate

Product 1

HCID 89812857HCID 89812857, compoundYield 62.8%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Methyl 1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxylate (500 mg, 1.56 mmol) and NaOH (375 mg, 9.38 mmol) were dissolved in H2O (13 mL), THF (13 mL) and MeOH (13 mL). After stirring for 2 hours at room temperature, H2O (30 mL) and EtOAc (30 mL) were added. To the stirred mixture was added 1 N hydrochloric acid until pH was 3. The layers were separated and the aqueous layer was extracted twice with EtOAc. The combined organic layers were dried over MgSO4, concentrated to give 300 mg of the title compound. MS: (−) m/z 305.26 (M−1).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted twice with EtOAc
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-04aa1abc4616406086e841edd2724bdd
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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