Sodium Carbonate → HCID 67040735, compound

HRID 883946Notes

Reaction equation

HRID 883946 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:27])[C:10]2[CH:15]=[CH:14][C:13]([O:16][C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=3)=[C:12]([N+:24]([O-])=O)[CH:11]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)(=O)C.C(O)C.O.[Fe]>[NH2:24][C:12]1[CH:11]=[C:10]([CH:15]=[CH:14][C:13]=1[O:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1)[C:9]([NH:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)=[O:27]

Participants

7

Reactant 2

HCID 10340Sodium CarbonateHCID 67040234HCID 67040234, compound

Product 1

HCID 67040735HCID 67040735, compoundYield 92.2%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of the product of Example 54B (116.6 mg, 0.2717 mmol) and iron powder (60.7 mg, 1.087 mmol) in acetic acid (2 mL) and ethanol (2 mL) was heated at reflux under a nitrogen atmosphere for 1 hour. The reaction was then cooled to room temperature. The mixture was diluted with water (20 mL), the pH adjusted to 6 with solid sodium carbonate, and the aqueous extracted with ethyl acetate (2×50 mL). The combined organic extracts were washed with brine (25 mL), dried over sodium sulfate, filtered, and concentrated under vacuum to provide the title compound as a beige solid (100 mg, 92%).

Workup

  1. temperatureat reflux under a nitrogen atmosphere for 1 hour
  2. extractionthe aqueous extracted with ethyl acetate (2×50 mL)
  3. washThe combined organic extracts were washed with brine (25 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-cacca206af8b4bfba86e97cf8cf33fc0
Source dataset
uspto-grants-2012_08
Patent number
US08236950B2

Reaction notes

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