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1,2-Dimethoxyethane → 3-(1-Isopropyl-7-methyl-1,2,3,4-tetrahydro-6-quinolinyl)-4-methoxybenzaldehyde

HRID 1057847
Notes
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Reaction equation

HRID 1057847 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH3:12])[N:8]([CH:13]([CH3:15])[CH3:14])[CH2:7][CH2:6][CH2:5]2.[C:16](=[O:19])([O-])[O-].[K+].[K+].CO[CH2:24][CH2:25][O:26][CH3:27]>O.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:13]([N:8]1[C:9]2[C:4](=[CH:3][C:2]([C:3]3[CH:2]=[C:11]([CH:10]=[CH:24][C:25]=3[O:26][CH3:27])[CH:16]=[O:19])=[C:11]([CH3:12])[CH:10]=2)[CH2:5][CH2:6][CH2:7]1)([CH3:15])[CH3:14]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 222683656-Bromo-1-isopropyl-7-methyl-1,2,3,4-tetrahydro-quinoline

Product 1

HCID 222682923-(1-Isopropyl-7-methyl-1,2,3,4-tetrahydro-6-quinolinyl)-4-methoxybenzaldehydeYield 79%

Reagents, catalysts & solvents 3

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 962WaterSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 6-bromo-1-isopropyl-7-methyl-1,2,3,4-tetrahydro-quinoline (0.85 g, 3.16 mmol), 2-methoxy-5-formyl boronic acid (1.13 g, 6.31 mmol) and potassium carbonate (1.70 g, 12.64 mmol) in 1,2-dimethoxyethane (30 mL) and water (1.5 mL) was degassed with argon for 15 minutes. Tetrakis(triphenylphosphine)palladium(0) (0.80 g, 0.63 mmol) was added and the mixture heated at reflux under argon for 35 hours. The solution was cooled to room temperature, diluted with ethyl acetate and washed successively with water and brine, dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was chromatographed and silica gel (eluent: ethyl acetate/hexane, 1:9) to give 0.81 g of 3-(1-isopropyl-7-methyl-1,2,3,4-tetrahydro-6-quinolinyl)-4-methoxybenzaldehyde (79%). 1H NMR (500 MHz; CDCl3): δ1.18 (s, 3H); 1.20 (s, 3H); 1.94 (m, 2H); 2.06 (s, 3H); 2.72 (m, 2H); 3.18 (m, 2H); 3.85 (s, 3H); 4.16 (m, 1H); 6.57 (s, 1H); 6.78 (s, 1H); 7.02 (d, 1H); 7.69 (d, 1H); 7.34 (s, 1H); 7.84 (m, 1H); 9.89 (s, 1H).

Workup

  1. customwas degassed with argon for 15 minutes
  2. temperaturethe mixture heated
  3. temperatureat reflux under argon for 35 hours
  4. washwashed successively with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was chromatographed

Sources & evidence

ORD record
ord-9ed5f2f96d0841be80b221081f00a5f2
Source dataset
uspto-grants-2003_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06515003B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes