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Sodium Hydroxide → 5-[3-(3,4-Dihydro-5-isoquinolinyl)-1,2,4-oxadiazol-5-yl]-2-[(1-methylethyl)oxy]benzonitrile

HRID 2383302
Notes
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Reaction equation

HRID 2383302 reaction equation
[CH3:1][CH:2]([O:4][C:5]1[CH:12]=[CH:11][C:10]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:27]=[CH:26][CH:25]=[C:24]4[C:19]=3[CH2:20][CH2:21][NH:22][CH2:23]4)[N:14]=2)=[CH:9][C:6]=1[C:7]#[N:8])[CH3:3].BrN1C(=O)CCC1=O.[OH-].[Na+]>C(Cl)Cl>[CH:23]1[C:24]2[C:19](=[C:18]([C:15]3[N:14]=[C:13]([C:10]4[CH:11]=[CH:12][C:5]([O:4][CH:2]([CH3:3])[CH3:1])=[C:6]([CH:9]=4)[C:7]#[N:8])[O:17][N:16]=3)[CH:27]=[CH:26][CH:25]=2)[CH2:20][CH2:21][N:22]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 67184N-bromobutanimideHCID 441248992-[(1-Methylethyl)oxy]-5-[3-(1,2,3,4-tetrahydro-5-isoquinolinyl)-1,2,4-oxadiazol-5-yl]benzonitrile

Product 1

HCID 595910795-[3-(3,4-Dihydro-5-isoquinolinyl)-1,2,4-oxadiazol-5-yl]-2-[(1-methylethyl)oxy]benzonitrileYield 96%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

A solution of 2-[(1-methylethyl)oxy]-5-[3-(1,2,3,4-tetrahydro-5-isoquinolinyl)-1,2,4-oxadiazol-5-yl]benzonitrile (Preparation 7, 50 mg, 0.139 mmol) and N-bromosuccinimide (29.6 mg, 0.166 mmol) in DCM (5 mL) was heated at reflux for 3 h, then cooled to room temperature. 2M aqueous NaOH (5 mL) was added, and the layers separated. The aqueous was extracted with DCM (5 mL) and the organic layers combined. Concentration in vacuo gave the title compound as a yellow solid (47.8 mg). 1H NMR (400 MHz, CDCl3) δ 8.52 (1H, t), 8.43 (1H, d), 8.34 (1H, dd), 8.23 (1H, dd), 7.55-7.51 (2H, m), 7.14 (1H, d), 4.81 (1H, sept), 3.86 (2H, td), 3.31 (2H, t), 1.48 (6H, d); m/z (ES) 359 [M+H]+.

Workup

  1. temperatureat reflux for 3 h
  2. customthe layers separated
  3. extractionThe aqueous was extracted with DCM (5 mL)
  4. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-06c8d64399604a5aa07ce0d115f155f8
Source dataset
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08263620B2

Reaction notes

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