3-Nitrophthalic anhydride → HCID 86660585, compound

HRID 718722Notes

Reaction equation

HRID 718722 reaction equation
Cl.[NH2:2][C:3]1([CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:25])[O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:8][CH2:7][C:6](=[O:9])[NH:5][C:4]1=[O:10].[N+:26]([C:29]1[CH:39]=[CH:38][CH:37]=[C:31]2[C:32]([O:34][C:35](=O)[C:30]=12)=[O:33])([O-:28])=[O:27].C([O-])(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(O)(=O)C>[N+:26]([C:29]1[CH:39]=[CH:38][CH:37]=[C:31]2[C:30]=1[C:35](=[O:34])[N:2]([C:3]1([CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:25])[O:17][CH2:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:8][CH2:7][C:6](=[O:9])[NH:5][C:4]1=[O:10])[C:32]2=[O:33])([O-:28])=[O:27]

Participants

6

Reactant 4

HCID 216313-Nitrophthalic anhydrideHCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 86660583HCID 86660583, compound

Product 1

HCID 86660585HCID 86660585, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
130 °C

Procedure

To a mixture of 4 (0.326 g, 0.881 mmol), 3-nitrophthalic anhydride (0.211 g, 1.093 mmol) and sodium acetate (0.097 g, 1.181 mmol) was added acetic acid (4.0 mL) and the resulting mixture was stirred overnight at 130° C. After 20 h, the mixture was carefully neutralized with sodium bicarbonate and extracted into DCM. The organic layer was dried over MgSO4, filtered, and concentrated. Purification by flash chromatography (95:5 DCM:MeOH) afforded 5 (0.241 g, 54%) as a white solid.

Workup

  1. waitAfter 20 h
  2. extractionextracted into DCM
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash chromatography (95:5 DCM:MeOH)

Sources & evidence

ORD record
ord-82bb98b96308467f88d144b4420f3a8e
Source dataset
uspto-grants-2015_11
Patent number
US09193989B2

Reaction notes

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