Sodium Hydroxide → HCID 19041719, compound

HRID 1684012Notes

Reaction equation

HRID 1684012 reaction equation
[Br:1][C:2]1[CH:30]=[CH:29][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]([C:18]3[CH:19]=[C:20]([CH:25]=[CH:26][CH:27]=3)[C:21]([O:23]C)=[O:22])=[C:8]2[CH3:28])=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[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]([C:18]3[CH:19]=[C:20]([CH:25]=[CH:26][CH:27]=3)[C:21]([OH:23])=[O:22])=[C:8]2[CH3:28])=[CH:29][CH:30]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19041710HCID 19041710, compound

Product 1

HCID 19041719HCID 19041719, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of the ester from Step 4 (445 mg, 0.96 mmol) and 2N NaOH (1.5 mL, 3 mmol) in ethanol (10 mL) was heated to reflux for 2 h then it was cooled and kept at 25° C. for 16 h. Ethanol was removed and the residue dissolved in water (20 mL). 1N HCl (5 mL) was added dropwise and under vigorous stirring; the solid was filtered and dried. A swish in Et2O/hexane mixture yielded the pure product (350 mg) Anal. calcd. for C24H20BrNO3 : C, 64.01; H, 4.48; N, 3.11. Found: C, 63.56; H, 4.35; N, 3.12.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 h
  3. temperatureit was cooled
  4. customEthanol was removed
  5. dissolutionthe residue dissolved in water (20 mL)
  6. addition1N HCl (5 mL) was added dropwise and under vigorous stirring
  7. filtrationthe solid was filtered
  8. customdried

Sources & evidence

ORD record
ord-3e6bf4dfa79042eab339e3802e24dcb4
Source dataset
uspto-grants-1997_06
Patent number
US05639780

Reaction notes

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