Sodium Hydroxide → HCID 19041680, compound

HRID 1684007Notes

Reaction equation

HRID 1684007 reaction equation
[Br:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([CH2:18][C:19]3[CH:28]=[CH:27][CH:26]=[CH:25][C:20]=3[C:21]([O:23]C)=[O:22])=[C:8]2[CH3:29])=[CH:4][CH:3]=1.[OH-].[Na+]>C1COCC1.CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([CH2:18][C:19]3[CH:28]=[CH:27][CH:26]=[CH:25][C:20]=3[C:21]([OH:23])=[O:22])=[C:8]2[CH3:29])=[CH:30][CH:31]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 19041704HCID 19041704, compound

Product 1

HCID 19041680HCID 19041680, compoundYield 51.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product of Step 2 (300 mg, 0.62 mmol) in THF (2 mL) and MeOH (4 mL) was added NaOH (3N, 0.62 mL). The mixture was refluxed for 2.5 h and then cooled to r.t. Acidification with 1N HCl followed by extraction with EtOAc gave 148 mg of the title compound after evaporation of solvent. Anal. calcd. for C25H22NO3Br --H2O: C, 63.43, H, 4.90; N, 2.96; found: C, 63.77; H, 4.89; N, 3.12.

Workup

  1. temperatureThe mixture was refluxed for 2.5 h
  2. extractionAcidification with 1N HCl followed by extraction with EtOAc

Sources & evidence

ORD record
ord-ea1df810ff37423782d07c456d269e69
Source dataset
uspto-grants-1997_06
Patent number
US05639780

Reaction notes

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