Sodium Hydroxide → HCID 59777540, compound

HRID 2401247Notes

Reaction equation

HRID 2401247 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([NH:20][C:21]2[CH:26]=[C:25]([CH3:27])[CH:24]=[CH:23][N:22]=2)[C:5]2[N:10]([CH2:11][CH2:12][O:13][CH2:14][CH3:15])[N:9]=[C:8]([C:16]([O:18]C)=[O:17])[C:6]=2[N:7]=1.[OH-].[Na+]>O1CCOCC1>[Cl:1][C:2]1[N:3]=[C:4]([NH:20][C:21]2[CH:26]=[C:25]([CH3:27])[CH:24]=[CH:23][N:22]=2)[C:5]2[N:10]([CH2:11][CH2:12][O:13][CH2:14][CH3:15])[N:9]=[C:8]([C:16]([OH:18])=[O:17])[C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58935563HCID 58935563, compound

Product 1

HCID 59777540HCID 59777540, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The ester of Step 7 (4.3 g, 11 mmol) was dissolved in dioxan (50 mL) and the solution treated with a 1M aqueous solution of sodium hydroxide (22.0 mL, 22.0 mmol). The reaction mixture was then stirred for 18 hours at room temperature. The reaction mixture was evaporated to dryness, the residue dissolved in water (100 mL) and washed with dichloromethane (50 mL). The aqueous phase was then acidified with 1M citric acid solution to pH 4-5 and a yellow precipitate formed. The mixture was stirred for 15 minutes before being filtered and the solid product dried in vacuo over phosphorus pentoxide to yield the title product, 3.75 g.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. dissolutionthe residue dissolved in water (100 mL)
  3. washwashed with dichloromethane (50 mL)
  4. customa yellow precipitate formed
  5. stirringThe mixture was stirred for 15 minutes
  6. filtrationbefore being filtered
  7. dry with materialthe solid product dried in vacuo over phosphorus pentoxide

Sources & evidence

ORD record
ord-4536f2108dca47b6979b2ff823b27952
Source dataset
uspto-grants-2014_08
Patent number
US08796288B2

Reaction notes

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