Formic Acid → 6-Bromo-4,4-dimethyl-3,4-dihydroquinoline-1(2H)-carbaldehyde

HRID 2185260Notes

Reaction equation

HRID 2185260 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH2:7][CH2:6][C:5]2([CH3:13])[CH3:12].[CH:14](O)=[O:15]>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH:14]=[O:15])[CH2:7][CH2:6][C:5]2([CH3:13])[CH3:12]

Participants

3

Reactant 2

HCID 284Formic AcidHCID 108239326-Bromo-1,2,3,4-tetrahydro-4,4-dimethylquinoline

Product 1

HCID 225688836-Bromo-4,4-dimethyl-3,4-dihydroquinoline-1(2H)-carbaldehydeYield 90%

Procedure

A solution of 6-bromo-4,4-dimethyl-1,2,3,4-tetrahydroquinoline, available in accordance with U.S. Pat. No. 5,089,509, the specification of which is incorporated herein by reference (1.8 g, 7.5 mmol) in 10 mL of formic acid was refluxed for 3 h. The reaction mixture was then led to ambient temperature and poured into ice-cold saturated aqueous sodium bicarbonate solution and extracted with diethyl ether (×2). The combined organic phase was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to a residue which was subjected to flash column chromatography over silica gel (230-400 mesh) using 15-25% ethyl acetate in hexane as the eluent to afford the title compound as a pale yellow solid (1.8 g, 90%).

Workup

  1. temperaturewas refluxed for 3 h
  2. customwas then led to ambient temperature
  3. additionpoured into ice-cold saturated aqueous sodium bicarbonate solution
  4. extractionextracted with diethyl ether (×2)
  5. dry with materialThe combined organic phase was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo to a residue which

Sources & evidence

ORD record
ord-3d86d165f1124f8280a9fbc4ce7eb035
Source dataset
uspto-grants-2002_06
Patent number
US06399774B1

Reaction notes

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