Sodium Hydroxide → 7-Cyanonaphthalene-2-carboxylic acid

HRID 2238421Notes

Reaction equation

HRID 2238421 reaction equation
[OH-].[Na+].[C:3]([C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[CH:10][C:11]([C:15]([O:17]C)=[O:16])=[CH:12]2)=[CH:7][CH:6]=1)#[N:4]>O.CCO.C(Cl)Cl>[C:3]([C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[CH:10][C:11]([C:15]([OH:17])=[O:16])=[CH:12]2)=[CH:7][CH:6]=1)#[N:4]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 23359864Methyl 7-cyano-2-naphthoate

Product 1

HCID 153922407-Cyanonaphthalene-2-carboxylic acidYield 99%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of NaOH (1.36 g, 34 mmol) in water (35 mL) was added dropwise to a solution of 191 (4.95 g, 24 mmol) in EtOH (100 mL) and CH2Cl2 (30 mL) and the mixture was stirred for 15 h. Water was added to dissolve the white solid and the mixture was extracted with CH2Cl2 (×2) and EtOAc. The aqueous portion was acidified (pH 2) with aqueous HCl (2N) and the resulting precipitate was filtered off, washed with water, and dried in a vacuum desiccator to give 7-cyano-2-naphthoic acid (192) (4.60 g, 99%), as a colorless powder: mp 279-283° C.; lit. mp [Aust. J. Chem., 1965, 18, 1351] 286-288° C.; 1H NMR [(CD3)2SO] δ 13.25 (br s, 1H), 8.81 (s, 1H), 8.75 (s, 1H), 8.20 (d, J=8.5 Hz, 1H), 8.17 (d, J=8.5 Hz, 2H), 8.15 (d, J=8.5 Hz, 2H), 7.92 (dd, J=8.5, 1.3 Hz, 1H).

Workup

  1. dissolutionto dissolve the white solid
  2. extractionthe mixture was extracted with CH2Cl2 (×2) and EtOAc
  3. filtrationthe resulting precipitate was filtered off
  4. washwashed with water
  5. customdried in a vacuum desiccator

Sources & evidence

ORD record
ord-a8d868e2ebff486ea031422f298e2372
Source dataset
uspto-grants-2010_05
Patent number
US07718688B2

Reaction notes

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