Hydrochloric Acid → HCID 22676732, compound

HRID 1006267Notes

Reaction equation

HRID 1006267 reaction equation
[Sn](Cl)Cl.[C:4]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([N+:23]([O-])=O)[CH:21]=3)[N:16]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([O:33][CH3:34])[CH:28]=3)[C:15]=2[C:35]([O:37][CH2:38][CH3:39])=[O:36])=[CH:10][CH:9]=1)([CH3:7])([CH3:6])[CH3:5].Cl.[OH-].[Na+]>CCO>[NH2:23][C:20]1[CH:21]=[C:22]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([O:33][CH3:34])[CH:28]=1)[C:15]([C:35]([O:37][CH2:38][CH3:39])=[O:36])=[C:14]2[C:11]1[CH:10]=[CH:9][C:8]([C:4]([CH3:5])([CH3:7])[CH3:6])=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 22676844HCID 22676844, compound

Product 1

HCID 22676732HCID 22676732, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

Tin (II) chloride (8.5 g, 45 mmol) was added to a stirred solution of ethyl 3-(4-tert-butylphenyl)-1-(3-methoxybenzyl)-5-nitro-1H-indole-2-carboxylate (Example 28, 4.5 g, 9.3 mmol) in EtOH (24 mL). The mixture was heated (50° C.) until there was a homogenous solution and then concentrated hydrochloric acid (16 mL) was added. The reaction was stirred at 60° C. for 2 h and then cooled. The pH of the solution was adjusted to pH=12 using 1 M aqueous sodium hydroxide and then the product was extracted with ethyl acetate (3×10 mL). The combined organic extracts were dried over anhydrous magnesium sulfate, and concentrated in vacuo to leave 2.8 g (67%) of crude product that was taken to the next reaction without as proceeded to the next step without further purification. Mass spectroscopy gave MH+=457.4 (exact mass calc'd for C29H32N2O4=456.24).

Workup

  1. temperaturecooled
  2. extractionthe product was extracted with ethyl acetate (3×10 mL)
  3. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto leave 2.8 g (67%) of crude product that
  6. customwas taken to the next reaction without
  7. customas proceeded to the next step without further purification
  8. customMass spectroscopy gave MH+=457.4 (exact mass calc'd for C29H32N2O4=456.24)

Sources & evidence

ORD record
ord-023dc138d26c4b2489f921320b7f5400
Source dataset
uspto-grants-2004_09
Patent number
US06787651B2

Reaction notes

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