Sodium Hydroxide → HCID 45089446, compound

HRID 644798Notes

Reaction equation

HRID 644798 reaction equation
[CH:1]([N:4]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[C:5]1[C:12]([O:14]CC)=[O:13])([CH3:3])[CH3:2].[OH-].[Na+]>C(O)C>[CH:1]([N:4]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[C:5]1[C:12]([OH:14])=[O:13])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 56931838HCID 56931838, compound

Product 1

HCID 45089446HCID 45089446, compoundYield 95,352.398%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 1-isopropyl-4-nitro-1H-pyrrole-2-carboxylate (656 mg, 2.900 mmol; see step (ii) above) was dissolved in ethanol (4 mL) to which was added a solution of NaOH (490 mg, 12.250 mmol in water (10 mL)). The reaction mixture was heated under reflux for 1.5 h and then the ethanol was removed under reduced pressure at 40° C. The reaction mixture was extracted with DCM (10 mL), and the water layer was collected, cooled to 0° C. with ice-water then acidified with HClconc with stirring. The white solid material precipitated was filtered off, washed with water and dried under reduced pressure at 50° C. to give the required product (548 g, 95% yield), m.p. 194-195° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 1.5 h
  3. customthe ethanol was removed under reduced pressure at 40° C
  4. extractionThe reaction mixture was extracted with DCM (10 mL)
  5. customthe water layer was collected
  6. customThe white solid material precipitated
  7. filtrationwas filtered off
  8. washwashed with water
  9. customdried under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-9a5e4a62b735446785c6727c07e2ea5e
Source dataset
uspto-grants-2010_04
Patent number
US07700765B2

Reaction notes

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