Sodium Hydroxide → 1-Cyano-4-methoxy-8-phenoxy-isoquinoline-3-carboxylic acid

HRID 706218Notes

Reaction equation

HRID 706218 reaction equation
C[O:2][C:3]([C:5]1[N:6]=[C:7]([C:24]#[N:25])[C:8]2[C:13]([C:14]=1[O:15][CH3:16])=[CH:12][CH:11]=[CH:10][C:9]=2[O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:4].[OH-].[Na+]>CO.O1CCCC1>[C:24]([C:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][C:9]=2[O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:14]([O:15][CH3:16])=[C:5]([C:3]([OH:4])=[O:2])[N:6]=1)#[N:25]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 671104881-Cyano-4-methoxy-8-phenoxy-isoquinoline-3-carboxylic acid methyl ester

Product 1

HCID 671101241-Cyano-4-methoxy-8-phenoxy-isoquinoline-3-carboxylic acidYield 92.7%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a mixture of 1-cyano-4-methoxy-8-phenoxy-isoquinoline-3-carboxylic acid methyl ester (727 mg, 2.18 mmol) and methanol/tetrahydrofuran (12.5 mL, 1:1.5) was added 2N sodium hydroxide (5.4 mL, 10.89 mmol) at room temperature. The yellow solution was stirred at that temperature for seventy minutes before it was concentrated. Water (20 mL) was added and the mixture was adjusted to pH=2 with 1N HCl (13 mL). The mixture was then extracted with dichloromethane and ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, concentrated in vacuo to give the title compound as a yellow solid (647 mg): MS: (+) m/z 320.80 (M+1).

Workup

  1. concentrationwas concentrated
  2. additionWater (20 mL) was added
  3. extractionThe mixture was then extracted with dichloromethane and ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8114a5f0191d4d979dca22b5211cd701
Source dataset
uspto-grants-2015_11
Patent number
US09174976B2

Reaction notes

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