Sodium Chloride → HCID 19603439, compound

HRID 1604579Notes

Reaction equation

HRID 1604579 reaction equation
[OH2:1].O.P([O-])(O)(O)=O.[Na+].CC(=CC)C.[CH2:14]([O:21][C:22]1[CH:23]=[CH:24][CH:25]=[C:26]2[C:31]=1[N:30]=[C:29]([CH3:32])[CH:28]=[C:27]2[CH:33]=[O:34])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Cl-].[Na+]>C(O)(C)(C)C.O>[CH2:14]([O:21][C:22]1[CH:23]=[CH:24][CH:25]=[C:26]2[C:31]=1[N:30]=[C:29]([CH3:32])[CH:28]=[C:27]2[C:33]([OH:1])=[O:34])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 105532-Methyl-2-buteneHCID 19603443HCID 19603443, compoundHCID 23673460Sodium Phosphate, Monobasic, Dihydrate

Product 1

HCID 19603439HCID 19603439, compoundYield 98.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

To a stirred solution of sodium dihydrogenphosphate dihydrate (788 mg) and 2-methyl-2-butene (885 mg) in tert-butanol (12 ml) and water (3 ml) was added 8-benzyloxy-4-formyl-2-methylquinoline (700 mg) and sodium chloride (79% purity, 457 mg) successively at ambient temperature. After being stirred for one and half an hour, the reaction was quenched with water (12 ml), then the pH of the mixture was adjusted to about 3-4 by addition of 1N hydrochloric acid. The mixture was extracted with chloroform and dried over anhydrous magnesium sulfate. The organic phase was concentrated in vacuo and the residual solid was triturated with diethyl ether to give 8-benzyloxy-4-carboxy-2-methylquinoline (729 mg, 98.5%) as a pale yellow powder.

Workup

  1. customthe reaction was quenched with water (12 ml)
  2. additionthe pH of the mixture was adjusted to about 3-4 by addition of 1N hydrochloric acid
  3. extractionThe mixture was extracted with chloroform
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationThe organic phase was concentrated in vacuo
  6. customthe residual solid was triturated with diethyl ether

Sources & evidence

ORD record
ord-e10bc1c7858a4ddb989b728eecd193aa
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

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