Hydrochloric Acid → 847955-92-4

HRID 1171475Notes

Reaction equation

HRID 1171475 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:10]([O:12]CC)=[O:11])[NH:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl>CO>[C:1]([C:5]1[CH:6]=[C:7]([C:10]([OH:12])=[O:11])[NH:8][CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21075144HCID 21075144, compound

Product 1

HCID 21075086847955-92-4Yield 88.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Ethyl 4-tert-butyl-1H-pyrrole-2-carboxylate (from C7, Step 1) (38 mg, 1.95 mmol, 1 eq), 1.000 N NaOH (39 mL, 39 mmol, 20 eq) and MeOH (50 mL) were mixed and refluxed for 1 hour. The mixture was acidified with 1.0 N HCl, (1.0 N), the MeOH stripped, and the remaining aqueous extracted with ethyl acetate (2×). The organic layers were combined, dried (MgSO4), and stripped to yield 290 mg of an off-white solid. NMR (CDCl3+2 drops DMSO-D6) δ 6.50 (s, 1H); 6.46 (s, 1H); 0.95 (s, 9H).

Workup

  1. temperaturerefluxed for 1 hour
  2. extractionthe remaining aqueous extracted with ethyl acetate (2×)
  3. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-ed9f770ea6e74e199414f93dbf2f0cce
Source dataset
uspto-grants-2010_11
Patent number
US07829571B2

Reaction notes

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