Hydrochloric Acid → HCID 53779105, compound

HRID 2268219Notes

Reaction equation

HRID 2268219 reaction equation
[CH3:1][C:2]1([CH3:29])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([CH:14]=[CH:15][C:16]([NH:18][C:19]3[CH:28]=[CH:27][CH:26]=[CH:25][C:20]=3[C:21]([O:23]C)=[O:22])=[O:17])[CH:5]=[CH:4][C:3]1=2.C1COCC1.[OH-].[Na+].Cl>O.CO>[CH3:1][C:2]1([CH3:29])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([CH:14]=[CH:15][C:16]([NH:18][C:19]3[CH:28]=[CH:27][CH:26]=[CH:25][C:20]=3[C:21]([OH:23])=[O:22])=[O:17])[CH:5]=[CH:4][C:3]1=2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 70215238HCID 70215238, compound

Product 1

HCID 53779105HCID 53779105, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

540 mg (1.38 mmol) of methyl 2-[3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)acryloylamino]benzoate, 5 ml of THF and 5 ml of methanol are introduced into a round-bottomed flask. 5.5 ml of methanolic sodium hydroxide solution (2N) are added and the mixture is stirred at room temperature for four hours. The reaction medium is poured into water, acidified to pH 1 with hydrochloric acid and extracted with ethyl acetate, and the organic phase is separated out after settling has taken place, washed with water, dried over magnesium sulphate and evaporated. The residue obtained is purified by chromatography on a column of silica eluted with a mixture of heptane and ethyl acetate (95/5). After evaporating the solvents, 400 mg (77%) of the expected acid, with a melting point of 185-6° C., are collected.

Workup

  1. extractionextracted with ethyl acetate
  2. customthe organic phase is separated out after settling
  3. washwashed with water
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customThe residue obtained
  7. customis purified by chromatography on a column of silica
  8. washeluted with a mixture of heptane and ethyl acetate (95/5)
  9. customAfter evaporating the solvents, 400 mg (77%) of the expected acid
  10. customwith a melting point of 185-6° C., are collected

Sources & evidence

ORD record
ord-8847880d928d42b5a43c82e903049d9f
Source dataset
uspto-grants-2001_12
Patent number
US06326510B1

Reaction notes

Loading…