Sodium hydride → HCID 54522152, compound

HRID 1265253Notes

Reaction equation

HRID 1265253 reaction equation
[CH3:1][C:2]1([CH3:19])[C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][C:6]=2[C:5]([CH3:18])([CH3:17])[CH2:4][CH2:3]1)[NH:13][C:12](=O)[CH2:11][CH2:10]3.[H-].[Na+].Br[CH2:23][C:24]1[CH:33]=[CH:32][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][CH:25]=1>C1COCC1>[CH3:31][O:30][C:28](=[O:29])[C:27]1[CH:32]=[CH:33][C:24]([CH2:23][N:13]2[C:14]3[C:9](=[CH:8][C:7]4[C:2]([CH3:19])([CH3:1])[CH2:3][CH2:4][C:5]([CH3:18])([CH3:17])[C:6]=4[CH:15]=3)[CH2:10][CH2:11][CH2:12]2)=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 256687Methyl 4-(bromomethyl)benzoateHCID 18614950HCID 18614950, compound

Product 1

HCID 54522152HCID 54522152, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of 6,6,9,9-tetramethyl-3,4,6,7,8,9-hexahydro-1H-benzo[g]quinolin-2-one (130 mg, 0.50 mmol) in THF (4 mL) was added NaH (18 mg, 0.76 mmol) in one portion at ambient temperature. To this solution was added methyl 4-(bromomethyl)-benzoate (229 mg, 1.01 mmol) in THF (8 mL). The mixture was then heated at 60° C. for 8 h, cooled to ambient temperature, quenched with aqueous saturated NH4Cl (20 mL), extracted with EtOAc (100 mL), dried with (MgSO4), concentrated, and purified by column chromatography (10% ether in hexane) to afford 4-(6,6,9,9-tetramethyl-3,4,6,7,8,9-hexahydro-1H-benzo[g]quinolin-1-ylmethyl)benzoic acid methyl ester (120 mg, 58%): 1H NMR (400 MHz, CDCl3) δ 8.10 (½ ABq, 2H, J=8.0 Hz, ArH), 7.48 (½ ABq, 2H, J=8.0 Hz, ArH), 7.08 (s, 1H, ArH), 6.70 (s, 1H, ArH), 5.20 (s, 2H, CH2), 4.51 (s, 3H, CH3), 2.91 (t, 2H, J=7.0 Hz, ring CH2), 2.81 (broad m, 2H, ring CH2), 1.60 (s, 4H, 2CH2), 1.23 (s, 12H, 4CH3).

Workup

  1. temperaturecooled to ambient temperature
  2. customquenched with aqueous saturated NH4Cl (20 mL)
  3. extractionextracted with EtOAc (100 mL)
  4. dry with materialdried with (MgSO4)
  5. concentrationconcentrated
  6. custompurified by column chromatography (10% ether in hexane)

Sources & evidence

ORD record
ord-139c3aa55f514407b57d0bff5ce1246d
Source dataset
uspto-grants-2003_04
Patent number
US06545049B1

Reaction notes

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