Water → Methyl 2-(4-(6-amino-1,3-dioxoisoindolin-5-yloxy)-3-chlorophenyl)acetate

HRID 2423323Notes

Reaction equation

HRID 2423323 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:23][C:24]([O:26][CH3:27])=[O:25])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][C:17]=1[N+:18]([O-])=O)[C:14](=[O:21])[NH:13][C:12]2=[O:22].O.O.Cl[Sn]Cl.O.C([O-])(O)=O.[Na+]>CCOC(C)=O>[NH2:18][C:17]1[CH:16]=[C:15]2[C:11]([C:12](=[O:22])[NH:13][C:14]2=[O:21])=[CH:10][C:9]=1[O:8][C:7]1[CH:6]=[CH:5][C:4]([CH2:23][C:24]([O:26][CH3:27])=[O:25])=[CH:3][C:2]=1[Cl:1]

Participants

6

Reactant 4

HCID 962WaterHCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 59864846Methyl 2-(3-chloro-4-(6-nitro-1,3-dioxoisoindolin-5-yloxy)phenyl)acetate

Product 1

HCID 59864779Methyl 2-(4-(6-amino-1,3-dioxoisoindolin-5-yloxy)-3-chlorophenyl)acetate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 30.1 (162 mg, 0.42 mmol) in 10 mL of EtOAc was added SnCl2.2H2O (469 mg, 2.1 mmol). The mixture was heated to reflux for 3 h. After cooling to room temperature, the mixture was poured into 20 mL of water. Saturated NaHCO3 was added to adjust the pH value of the mixture to 3. The mixture was filtered through Celite to remove solid precipitates. The filtrate was extracted with EtOAc. The EtOAc extract was washed with brine, dried over Na2SO4, and evaporated in vacuo to give 30.2. MS ESI (pos.) m/e calcd for (M+H)+ 361.1. found 361.0.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 h
  3. filtrationThe mixture was filtered through Celite
  4. customto remove solid
  5. customprecipitates
  6. extractionThe filtrate was extracted with EtOAc
  7. extractionThe EtOAc extract
  8. washwas washed with brine
  9. dry with materialdried over Na2SO4
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-5d32fd80df314b37bbaef1d7198c97b5
Source dataset
uspto-grants-2011_06
Patent number
US07960567B2

Reaction notes

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