Acetyl chloride → HCID 14988478, compound

HRID 1198476Notes

Reaction equation

HRID 1198476 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 1N 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-5d82a71971ca4e7b92c1832ff4fd2fd5
Source dataset
uspto-grants-1994_01
Patent number
US05281600

Reaction notes

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