Potassium Carbonate → HCID 21103673, compound

HRID 1354816Notes

Reaction equation

HRID 1354816 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:15]=[CH:14][C:10]=1[C:11](O)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[NH2:32][C:33]1[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][C:34]=1[OH:42]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:17]=[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:15]=[CH:14][C:10]=1[C:11]([NH:32][C:33]1[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][C:34]=1[OH:42])=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 49847212-Amino-5-NitrophenolHCID 9840634HCID 9840634, compound

Product 1

HCID 21103673HCID 21103673, compoundYield 55.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 37 (1 g, 3 mmol) was dissolved in THF (100 mL). K2CO3 (2 g, 15 mmol) was added followed by 2-amino-5-nitro-phenol (693 mg, 4.5 mmol). The reaction mixture was allowed to stir at room temperature overnight. K2CO3 was filtered off though filter paper. The solvent was removed under reduced pressure. Liquid-liquid extraction was performed using CHCl3 (100 mL) and H2O (50 mL). The organic layer was dried over MgSO4. After MgSO4 was filtered off, the solvent was removed under reduced pressure. The residue was purified by flash chromatography to give compound 39 (786 mg, 55.7% isolated yield). LC-MS (ESI): m/e=471.1 [M+1]+

Workup

  1. filtrationK2CO3 was filtered off
  2. filtrationthough filter paper
  3. customThe solvent was removed under reduced pressure
  4. extractionLiquid-liquid extraction
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationAfter MgSO4 was filtered off
  7. customthe solvent was removed under reduced pressure
  8. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-8eb5f4626103447eb753bebe8770a720
Source dataset
uspto-grants-2007_05
Patent number
US07223759B2

Reaction notes

Loading…