Sodium Hydroxide → HCID 18918218, compound

HRID 864792Notes

Reaction equation

HRID 864792 reaction equation
[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:18]C)[CH:16]=2)[C:11](=[O:20])[C:10]([N:21]2[CH2:26][CH2:25][N:24]([C:27]3[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=3)[CH2:23][CH2:22]2)=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br.[OH-].[Na+]>ClCCl>[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([OH:18])[CH:16]=2)[C:11](=[O:20])[C:10]([N:21]2[CH2:26][CH2:25][N:24]([C:27]3[CH:28]=[CH:29][N:30]=[CH:31][CH:32]=3)[CH2:23][CH2:22]2)=[CH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25134Boron tribromide2×HCID 18918418HCID 18918418, compound

Product 1

HCID 18918218HCID 18918218, compoundYield 9.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of the product of step (vi) (815 mg) in dry dichloromethane (10 ml) under argon was added a 1M solution of boron tribromide in dichloromethane (10 ml). The reaction was stirred at room temperature for 14 days, extra aliquots of BBr3 solution being added after 3 and 7 days. After 2 weeks, excess 1M aqueous sodium hydroxide solution was added, dropwise at first, and the mixture stirred at room temperature for 3 hours. The precipitated material was filtered off and the aqueous layer of the filtrate separated. The pH of the aqueous layer was adjusted to 8 by addition of 2N HCl (aq.) and 1M NaHCO3 (aq.) before being extracted with ethyl acetate. The organic extracts were washed with brine, dried (MgSO4) and evaporated to dryness to yield 1-benzyl-3-(4-(4-pyridyl)piperazin-1-yl)-4-quinolon-7-ol (75 mg) as an off-white solid: m.p. 141°-6° C. NMR (d6DMSO) δ3.10 (4H, m), 3.50 (4H, m), 5.40 (2H, s), 6.67 (1H, d), 6.72 (1H, dd), 6.90 (2H, m), 7.30 (5H, m), 7.76 (1H, s), 8.07 (1H, d), 8.15 (2H, s), 10.15 (1H, br, s); m/Z 413 (M+H)+.

Workup

  1. waitAfter 2 weeks
  2. stirringdropwise at first, and the mixture stirred at room temperature for 3 hours
  3. filtrationThe precipitated material was filtered off
  4. customthe aqueous layer of the filtrate separated
  5. additionThe pH of the aqueous layer was adjusted to 8 by addition of 2N HCl (aq.) and 1M NaHCO3 (aq.)
  6. extractionbefore being extracted with ethyl acetate
  7. washThe organic extracts were washed with brine
  8. dry with materialdried (MgSO4)
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-4ff28b691990434eae067846f26e6b4e
Source dataset
uspto-grants-1996_10
Patent number
US05563141

Reaction notes

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