Hydrochloric Acid → HCID 19784136, compound

HRID 257267Notes

Reaction equation

HRID 257267 reaction equation
[CH2:1]([C:3]1[N:4]=[C:5]2[C:10]([CH3:11])=[CH:9][C:8]([CH3:12])=[N:7][N:6]2[C:13]=1[CH2:14][C:15]1[CH:33]=[CH:32][C:18]([O:19][CH:20]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=2)[C:21]([O:23]C)=[O:22])=[CH:17][CH:16]=1)[CH3:2].[OH-].[Na+].Cl>CO>[CH2:1]([C:3]1[N:4]=[C:5]2[C:10]([CH3:11])=[CH:9][C:8]([CH3:12])=[N:7][N:6]2[C:13]=1[CH2:14][C:15]1[CH:16]=[CH:17][C:18]([O:19][CH:20]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=2)[C:21]([OH:23])=[O:22])=[CH:32][CH:33]=1)[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 19784144HCID 19784144, compound

Product 1

HCID 19784136HCID 19784136, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 0.043 g (0.09 mmol) of the product of Step A in 1 mL of methanol was added 0.5 mL of a 1.0N solution of sodium hydroxide and the reaction mixture was stirred at room temperature for 15 hours. The reaction mixture was then adjusted to pH=6 with 0.5 mL of 1.0N hydrochloric acid, then concentrated in vacuo. The residue was purified on a silica gel flash chromatography column eluted with CHCl3 -MeOH-NH4OH (80:15:1). The purified fractions were combined, evaporated and dried in vacuo to afford 0.028 g (67%) of the title compound.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified on a silica gel flash chromatography column
  3. washeluted with CHCl3 -MeOH-NH4OH (80:15:1)
  4. customevaporated
  5. customdried in vacuo

Sources & evidence

ORD record
ord-583df0511ec442a68b7a23e0097543b0
Source dataset
uspto-grants-1993_11
Patent number
US05260285

Reaction notes

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