Acetyl chloride → HCID 14988478, compound

HRID 1031921Notes

Reaction equation

HRID 1031921 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([C:12]([OH:14])=[O:13])[CH:11]=1)[NH:8][CH2:7][CH2:6][CH2:5]2.[OH-].[Na+].[C:17](Cl)(=[O:19])[CH3:18]>O1CCOCC1>[C:17]([NH:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([C:12]([OH:14])=[O:13])[CH:11]=1)[NH:8][CH2:7][CH2:6][CH2:5]2)(=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 14798Sodium HydroxideHCID 149884736-Amino-1,2,3,4-tetrahydroquinoline-8-carboxylic acid

Product 1

HCID 14988478HCID 14988478, compoundYield 16.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 6-amino-1,2,3,4-tetrahydroquinoline-8-carboxylic acid (4.80 g) in dioxane (60 ml) was added 1 N aqueous sodium hydroxide solution (60 ml) and acetyl chloride (2.5 ml), the mixture was stirred for 8 hours at room temperature. After salting out, extracted with ethyl acetate, washed with water and saturated aqueous sodium chloride solution successively and dried over anhydrous sodium sulfate. After solvent was distilled away and the resulting residue was purified by silica gel column chromatography eluting with dichloromethane-ethanol (9:1) to yield 0.98 g (16.8%) of the title compound. This compound was recrystallized from ethanol to give yellow crystals, mp 258°-259° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water and saturated aqueous sodium chloride solution successively
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationAfter solvent was distilled away
  5. customthe resulting residue was purified by silica gel column chromatography
  6. washeluting with dichloromethane-ethanol (9:1)

Sources & evidence

ORD record
ord-20cdb950c20a4fd9a77d1ddf85a786cf
Source dataset
uspto-grants-1990_09
Patent number
US04956372

Reaction notes

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