Ethyl Bromide → 2-(3-Ethoxyphenyl)-4,5-dihydropyrazolo[1,5-a]quinoline

HRID 2398082Notes

Reaction equation

HRID 2398082 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:20]=[C:11]3[CH2:12][CH2:13][C:14]4[C:19]([N:10]3[N:9]=2)=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH:5]=[CH:6][CH:7]=1.[Na].[CH2:22](Br)[CH3:23]>C(O)C>[CH2:22]([O:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:20]=[C:11]3[CH2:12][CH2:13][C:14]4[C:19]([N:10]3[N:9]=2)=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH:5]=[CH:6][CH:7]=1)[CH3:23]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 3042689Phenol, 3-(4,5-dihydropyrazolo(1,5-a)quinolin-2-yl)-HCID 5360545Sodium

Product 1

HCID 134125132-(3-Ethoxyphenyl)-4,5-dihydropyrazolo[1,5-a]quinoline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.62 Grams (0.010 mole) of the compound of Example 10 is added to a solution of 0.23 g. (0.010 mole) of sodium in 40 ml. of absolute ethanol at room temperature, then 2.2 g. (0.020 mole) of ethyl bromide is added dropwise. The resulting solution is refluxed for seven hours and allowed to stand overnight at room temperature. After dilution with 30 ml. of water and subsequent evaporation of the ethanol, a residue is obtained which is crystallized from methanol. Yield 2.29 g. of the title compound, m.p. 99°-100° C.

Workup

  1. customat room temperature
  2. temperatureThe resulting solution is refluxed for seven hours
  3. customof water and subsequent evaporation of the ethanol
  4. customa residue is obtained which
  5. customis crystallized from methanol

Sources & evidence

ORD record
ord-5ee4a91051b24501ab41c0447622520e
Source dataset
uspto-grants-1977_05
Patent number
US04024149

Reaction notes

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