Hydrochloric Acid → HCID 22452685, compound

HRID 2185882Notes

Reaction equation

HRID 2185882 reaction equation
[C:1]([C:3]1[C:4]([O:17][CH3:18])=[C:5]([C:13]([O:15]C)=[O:14])[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=2[CH:12]=1)#[N:2].[OH-].[Na+].C(=O)(O)[O-].[Na+].Cl>C1COCC1.O.CCOCC.CO>[C:1]([C:3]1[C:4]([O:17][CH3:18])=[C:5]([C:13]([OH:15])=[O:14])[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=2[CH:12]=1)#[N:2]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 22452663HCID 22452663, compound

Product 1

HCID 22452685HCID 22452685, compoundYield 19%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 3-cyano-2-methoxy-5,6,7,8-tetrahydro-1-naphthalenecarboxylate (0.65 g, 2.64 mmol) in THF (12 mL) and H2O (4 mL) was added 1N NaOH (3 mL). Methanol was added dropwise until the cloudy solution became clear. After stirring for 96 h at room temperature, the reaction was treated with sat. aqueous sodium bicarbonate and Et2O. The collected aqueous layer was acidified to pH 2 with 1N HCl, the resulting precipitate extracted with DCM (3×25 mL), dried (Na2SO4), filtered and concentrated to afford a white solid (0.115 g, 19%). 1H NMR (CDCl3) δ 7.39 (s, 1H), 4.09 (s, 3H), 2.82 (m, 4H), 1.80 (m, 4H).

Workup

  1. extractionthe resulting precipitate extracted with DCM (3×25 mL)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b20ef5d8f8ef4667a73f08e441aa942f
Source dataset
uspto-grants-2002_06
Patent number
US06403601B1

Reaction notes

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