Methanol → HCID 89812857, compound

HRID 1481070Notes

Reaction equation

HRID 1481070 reaction equation
C[O:2][C:3]([C:5]1[N:6]=[C:7]([C:23]#[N:24])[C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:9]=2)=[O:4].[OH-].[Na+].CO>C1COCC1>[C:23]([C:7]1[C:8]2[C:13](=[CH:12][CH:11]=[C:10]([O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:9]=2)[C:14]([OH:15])=[C:5]([C:3]([OH:4])=[O:2])[N:6]=1)#[N:24]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 89812860Methyl 1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxylate

Product 1

HCID 89812857HCID 89812857, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (140 mg, 0.44 mmol), 2 M NaOH (3 mL), MeOH (3 mL) and THF (3 mL) was stirred for 5 h at r.t. The resulting mixture was concentrated to approximately one-third of its original volume and then placed in an ice bath. Hydrochloric acid (1 M) was added until pH ˜2, and the mixture was extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated to give 132 mg of the title compound as a white solid. MS: (−) m/z 305.26 (M−1).

Workup

  1. concentrationThe resulting mixture was concentrated to approximately one-third of its original volume
  2. customplaced in an ice bath
  3. additionHydrochloric acid (1 M) was added until pH ˜2
  4. extractionthe mixture was extracted with EtOAc
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2f5ee083c8b848fea68716a227d26d4a
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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