Acetic Anhydride → HCID 13577653, compound

HRID 1589258Notes

Reaction equation

HRID 1589258 reaction equation
[Br:1][C:2]1[C:11]([F:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH:6]([CH3:13])[NH:7]2.[OH-].[Na+].[C:16](OC(=O)C)(=[O:18])[CH3:17]>S(=O)(=O)(O)O>[C:16]([N:7]1[C:8]2[C:3](=[C:2]([Br:1])[C:11]([F:12])=[CH:10][CH:9]=2)[CH2:4][CH2:5][CH:6]1[CH3:13])(=[O:18])[CH3:17]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 128968175-Bromo-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline

Product 1

HCID 13577653HCID 13577653, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Conditions

Temperature
20 °C

Procedure

To 6.0 g of 5-bromo-6-fluoro-1,2,3,4-tetrahydroquinaldine was added 50 ml of acetic anhydride and one drop of concentrated sulfuric acid. The solution was heated on a steam bath for two hours, then cooled to about 20° C. The solution was basified with 10% sodium hydroxide solution. The solution was extracted with chloroform, and the chloroform extracts were evaporated to provide an oil which was distilled in vacuo to provide N-acetyl-5-bromo-6-fluoro-1,2,3,4-tetrahydroquinaldine. The structural assignment was supported by nuclear magnetic resonance spectral analysis.

Workup

  1. temperatureThe solution was heated on a steam bath for two hours
  2. extractionThe solution was extracted with chloroform
  3. customthe chloroform extracts were evaporated
  4. customto provide an oil which
  5. distillationwas distilled in vacuo

Sources & evidence

ORD record
ord-3462e399414a4d8297a1331466a7eb8c
Source dataset
uspto-grants-1986_02
Patent number
US04568750

Reaction notes

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