Water → 4-[(2-Ethyl-5,6,7,8-tetrahydroquinolin-4-yl)oxymethyl]phenylboronic acid

HRID 1614771Notes

Reaction equation

HRID 1614771 reaction equation
[H-].[Na+].[CH2:3]([C:5]1[NH:6][C:7]2[CH2:8][CH2:9][CH2:10][CH2:11][C:12]=2[C:13](=[O:15])[CH:14]=1)[CH3:4].Br[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([B:24]([OH:26])[OH:25])=[CH:20][CH:19]=1.O>CN(C=O)C>[CH2:3]([C:5]1[CH:14]=[C:13]([O:15][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([B:24]([OH:26])[OH:25])=[CH:20][CH:19]=2)[C:12]2[CH2:11][CH2:10][CH2:9][CH2:8][C:7]=2[N:6]=1)[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27355934-(Bromomethyl)phenylboronic acidHCID 149504752-Ethyl-5,6,7,8-tetrahydroquinolin-4(1H)-one

Product 1

HCID 151714224-[(2-Ethyl-5,6,7,8-tetrahydroquinolin-4-yl)oxymethyl]phenylboronic acidYield 99.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% dispersion in oil; 180 mg) was added to a mixture of 2-ethyl-5,6,7,8-tetrahydro-4(1H)-quinolone (660 mg) and 4-bromomethylphenylboronic acid (800 mg) (obtained as described in J. Amer. Chem. Soc. 1958, 80, 835) in DMF (12 ml) under an atmosphere of argon. The mixture was stirred for 40 hours and then water (0.2 ml) was added. Volatile material was removed by evaporation and the residue was dissolved in warm 0.5M sodium hydroxide solution (10 ml). Insoluble material was removed by filtration and the filtrate was acidified to pH 4 with 20% citric acid solution. The precipitate solid was collected by filtration, washed with water (20 ml) and dried under high vacuum to give 4-[(2-ethyl-5,6,7,8-tetrahydroquinolin-4-yl)oxymethyl]phenylboronic acid (C) (1.15 g), m.p. 229°-231° C.; NMR (d6 -DMSO): 1.3(t,3H), 1.6-1.9(m,4H), 2.5-2.7(m,2H), 2.75-2.95(m,4H), 5.4(s,2H), 7.3(d,2H), 7.4(s,1H, 7.5(d,2H).

Workup

  1. customVolatile material was removed by evaporation
  2. dissolutionthe residue was dissolved in warm 0.5M sodium hydroxide solution (10 ml)
  3. customInsoluble material was removed by filtration
  4. filtrationThe precipitate solid was collected by filtration
  5. washwashed with water (20 ml)
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-047f4b2e36604a00a8e9a1dfa19e7bdd
Source dataset
uspto-grants-1993_03
Patent number
US05198439

Reaction notes

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