Sodium Hydroxide → HCID 19958580, compound

HRID 373782Notes

Reaction equation

HRID 373782 reaction equation
C([O:3][C:4]([CH2:6][N:7]1[C:16]2[C:11](=[CH:12][C:13]([Cl:18])=[CH:14][C:15]=2[Cl:17])[NH:10][C:9](=[O:19])[C:8]1=[O:20])=[O:5])C.[OH-].[Na+]>C1COCC1.O>[C:4]([CH2:6][N:7]1[C:16]2[C:11](=[CH:12][C:13]([Cl:18])=[CH:14][C:15]=2[Cl:17])[NH:10][C:9](=[O:19])[C:8]1=[O:20])([OH:5])=[O:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 19808460HCID 19808460, compound

Product 1

HCID 19958580HCID 19958580, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The ester of example 21 (34 mg, 0.107 mmol) was reacted with 0.1M NaOH (3.2 ml) in a mixture of THF (2.0 ml) and water (0,5 ml) for 26 h at 45° C. The solvent was removed in vacuo and the remanens was dissolved in water (1.0 ml), cooled in an ice bath and the pH was adjusted to 2.5 with 0.5 M hydrochloric acid. The precipitate was filtered off, washed with water and dried to give 20 mg (65%) of the title compound. 1H-NMR (DMSO-d6):δ5.0 (s, 2H), 7.2 (d, 1H), 7.41 (d, 1H), 12.33 (s, 1H), 13.18 (br.s, 1H).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe remanens was dissolved in water (1.0 ml)
  3. temperaturecooled in an ice bath
  4. filtrationThe precipitate was filtered off
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-91a8d8bce7ff4f2c86bd69fb0cacfade
Source dataset
uspto-grants-1992_11
Patent number
US05166155

Reaction notes

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