Sodium Hydroxide → HCID 19001361, compound

HRID 2259595Notes

Reaction equation

HRID 2259595 reaction equation
[CH2:1]([C:5]1[N:10]=[C:9]([Cl:11])[C:8]([CH2:12][C:13]([O:15]CC)=[O:14])=[C:7]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]([O:27]C)=[O:26])=[CH:21][CH:20]=2)[N:6]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+]>C(O)C>[CH2:1]([C:5]1[N:10]=[C:9]([Cl:11])[C:8]([CH2:12][C:13]([OH:15])=[O:14])=[C:7]([CH2:18][C:19]2[CH:20]=[CH:21][C:22]([C:25]([OH:27])=[O:26])=[CH:23][CH:24]=2)[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 88434916HCID 88434916, compound

Product 1

HCID 19001361HCID 19001361, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

220 mg of the product of Example 1 were introduced into 6.6 ml of ethanol and 0.6 ml of sodium hydroxide and after stirring at ambient temperature for 3 days and followed by evaporation to dryness under reduced pressure at a temperature below 40° C., the residue was dissolved in 2 ml of water and neutralized by the addition of approximately 0.6 ml of 2N hydrochloric acid. After separating and washing with water, 160 mg of product were obtained which was crystallized from 5 ml of hot isopropanol with 5 ml of water added to it. After 24 hours at 0°+5° C., 90 mg were separated and crystallized from 9 ml of ethyl acetate at reflux. After standing at rest for 24 hours, separation took place to obtain 46 mg of the expected product melting at approx. 205° C.

Workup

  1. customfollowed by evaporation to dryness under reduced pressure at a temperature below 40° C.
  2. dissolutionthe residue was dissolved in 2 ml of water
  3. additionneutralized by the addition of approximately 0.6 ml of 2N hydrochloric acid
  4. customAfter separating
  5. washwashing with water

Sources & evidence

ORD record
ord-30b2cf4dfd354abfadcae2010544444c
Source dataset
uspto-grants-1995_12
Patent number
US05474996

Reaction notes

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