Water → HCID 67392410, compound

HRID 907371Notes

Reaction equation

HRID 907371 reaction equation
C([O:3][C:4]([C:6]1[N:7]([CH3:22])[CH:8]=[C:9](/[CH:11]=[CH:12]/[C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)[CH:10]=1)=[O:5])C.C1COCC1.O.[OH-].[Na+]>C(O)C>[CH3:22][N:7]1[CH:8]=[C:9](/[CH:11]=[CH:12]/[C:13]2[CH:14]=[CH:15][C:16]([N+:19]([O-:21])=[O:20])=[CH:17][CH:18]=2)[CH:10]=[C:6]1[C:4]([OH:5])=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 67393245HCID 67393245, compound

Product 1

HCID 67392410HCID 67392410, compoundYield 55.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl-1-methyl-4-[(E)-2-(4-nitrophenyl)ethenyl]-1H-pyrrole-2-carboxylate (0.100 mg, 0.333 mmol; see step (ii) above) was suspended in ethanol (4 mL), THF (8 mL) and water (20 mL) to which sodium hydroxide solution (NaOH 0.190 g, 4.75 mmol in water 10 mL) was added with stirring. The reaction mixture was heated under reflux for 4 h. The reaction mixture was cooled to room temperature then HCl(conc.) was added dropwise with vigorous stirring until pH 2 was attained. The yellow, solid material was filtered off, washed with water and dried in vacuo at 60° C. to provide the title compound (50 mg, 55%), m.p.=212-215° C. (decomposition).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 4 h
  3. stirringwith vigorous stirring until pH 2
  4. filtrationThe yellow, solid material was filtered off
  5. washwashed with water
  6. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-72e5ebff8d364e68904c10f7114ec8c1
Source dataset
uspto-grants-2011_09
Patent number
US08012967B2

Reaction notes

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