Water → HCID 11117771, compound

HRID 1355377Notes

Reaction equation

HRID 1355377 reaction equation
[CH3:1][O:2][C:3]1[C:12]([C:13]#[N:14])=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]=1[C:15]([O:17]C)=[O:16].O[Li].O.C1COCC1.O>C(=O)(O)[O-].[Na+].CO>[CH3:1][O:2][C:3]1[C:12]([C:13]#[N:14])=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]=1[C:15]([OH:17])=[O:16]

Participants

7

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 11746770methyl 2-methoxy-3-cyano-1-naphthoate

Product 1

HCID 11117771HCID 11117771, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of methyl 2-methoxy-3-cyano-1-naphthoate (0.113 g), LiOH.H2O (0.0196 g), THF (3 mL), water (1 mL) and methanol (1 mL) was stirred overnight at room temperature. The solution was diluted with saturated sodium bicarbonate and extracted with Et2O. The aqueous layer was acidified to pH 2 by addition of 1N HCl and extracted with Et2O. The organic layer was washed with water (30 mL) and brine (40 mL), dried (sodium sulfate), filtered, and concentrated to a white solid. 1H NMR (DMSO-d6): δ14.06 (broad, 1H), 8.08-8.02 (m, 1H), 7.83-7.76 (m, 2H), 7.69-7.63 (m, 1H), 4.02 (s, 3H) MS m/z: 226 (M-1).

Workup

  1. extractionextracted with Et2O
  2. additionThe aqueous layer was acidified to pH 2 by addition of 1N HCl
  3. extractionextracted with Et2O
  4. washThe organic layer was washed with water (30 mL) and brine (40 mL)
  5. dry with materialdried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated to a white solid

Sources & evidence

ORD record
ord-e3de2be542494d4b87df24d99c2f1a7a
Source dataset
uspto-grants-2003_07
Patent number
US06586432B2

Reaction notes

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