Sodium Hydroxide → HCID 21949787, compound

HRID 2114665Notes

Reaction equation

HRID 2114665 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:22]=[C:23]([Cl:25])[CH:24]=1)[O:7][C:8]1[C:9]([CH2:20][CH3:21])=[N:10][N:11]([CH2:15][C:16]([O:18]C)=[O:17])[C:12]=1[CH2:13][CH3:14]>O1CCCC1>[Cl:3][C:4]1[CH:5]=[C:6]([CH:22]=[C:23]([Cl:25])[CH:24]=1)[O:7][C:8]1[C:9]([CH2:20][CH3:21])=[N:10][N:11]([CH2:15][C:16]([OH:18])=[O:17])[C:12]=1[CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10291825HCID 10291825, compound

Product 1

HCID 21949787HCID 21949787, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Aqueous sodium hydroxide solution (1N, 6.2 ml, 6.2 mmol) was added dropwise to a stirred solution of the ester (2 g, 5.6 mmol) of Example 9 in tetrahydrofuran (20 ml) at 0° C. After 1 hour the solvent was removed under reduced pressure and aqueous hydrochloric acid (20 ml) was added with vigorous stirring. The resulting white precipitate was collected by filtration, washed with ether (3×30 ml) and dried in a vacuum pistol at 60° C./10 mmHg to afford the title compound as a white solid (1.5 g), m.p. 157-158° C.

Workup

  1. customAfter 1 hour the solvent was removed under reduced pressure and aqueous hydrochloric acid (20 ml)
  2. additionwas added with vigorous stirring
  3. filtrationThe resulting white precipitate was collected by filtration
  4. washwashed with ether (3×30 ml)
  5. customdried in a vacuum pistol at 60° C./10 mmHg

Sources & evidence

ORD record
ord-42bf359bebe9415aa6692f8299d86d6e
Source dataset
uspto-grants-2008_10
Patent number
US07435728B2

Reaction notes

Loading…