Hydrochloric Acid → HCID 25109628, compound

HRID 1698411Notes

Reaction equation

HRID 1698411 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:16]([OH:30])[C:17]#[C:18][C:19]2[CH:28]=[CH:27][C:22]([C:23]([O:25]C)=[O:24])=[C:21]([OH:29])[CH:20]=2)[CH:8]=[CH:9][C:10]=1[N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])([CH3:4])([CH3:3])[CH3:2].[Cl-].[NH4+].Cl>C1COCC1.CO>[C:1]([C:5]1[CH:6]=[C:7]([CH:16]([OH:30])[C:17]#[C:18][C:19]2[CH:28]=[CH:27][C:22]([C:23]([OH:25])=[O:24])=[C:21]([OH:29])[CH:20]=2)[CH:8]=[CH:9][C:10]=1[N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 67276336HCID 67276336, compound

Product 1

HCID 25109628HCID 25109628, compoundYield 44.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.7 g (4.3 mmol) of methyl 4-[3-(3-tert-butyl-4-diethylaminophenyl)-3-hydroxyprop-1-ynyl]-2-hydroxybenzoate are dissolved in 50 ml of THF with 1 ml of methanol and 2 ml of 1N aqueous NaCH. The solution is stirred at ambient temperature for 2 hours and then 2 days at reflux. The reaction medium is poured into a saturated solution of ammonium chloride, and the aqueous phase is brought to acidic pH with 1N HCl and then extracted twice with ethyl acetate. The organic phase is dried over magnesium sulphate and then concentrated to dryness. The residue is purified by chromatography (heptane/ethyl acetate: 50/50). 760 mg of 4-[3-(3-tert-butyl-4-diethylaminophenyl)-3-hydroxy-prop-1-ynyl]-2-hydroxybenzoic acid are obtained in the form of a whitish solid (Mp=245° C., yield=45%).

Workup

  1. temperature2 days at reflux
  2. extractionextracted twice with ethyl acetate
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. concentrationconcentrated to dryness
  5. customThe residue is purified by chromatography (heptane/ethyl acetate: 50/50)

Sources & evidence

ORD record
ord-91c96eb8c6f843538932dab047e43779
Source dataset
uspto-grants-2012_04
Patent number
US08163952B2

Reaction notes

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