Dichloromethane → HCID 86687925, compound

HRID 2401462Notes

Reaction equation

HRID 2401462 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[N+:12]([O-])=O)[C:8](=[O:15])[N:7]([CH3:16])[CH2:6]2.O.O.Cl[Sn]Cl.C(Cl)Cl.[OH-].[Na+]>C(O)C.O>[NH2:12][C:11]1[CH:10]=[C:9]2[C:5]([CH2:6][N:7]([CH3:16])[C:8]2=[O:15])=[CH:4][C:3]=1[O:2][CH3:1]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 86687922HCID 86687922, compound

Product 1

HCID 86687925HCID 86687925, compoundYield 97.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

To crude 5-methoxy-2-methyl-6-nitroisoindolin-1-one (121 mg, 0.54 mmol) in ethanol (6 mL) and water (0.6 mL) was added SnCl2.2H2O (487 mg, 2.16 mmol) and the mixture was heated to 65° C. for 24 h. DCM (10 mL) and 2M NaOH(aq) (10 mL) were added and the mixture was passed through a hydrophobic frit. The solvent was removed in vacuo to give impure 6-amino-5-methoxy-2-methylisoindolin-1-one (101 mg, 97%) as an off-white solid. The crude material was used directly in the next reaction without any further purification. LCMS (10 cm_ESCI_Formic_MeCN): [M+H]+=193 at 2.00 min.

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-96997cbe338543dea704dc9b4cc32783
Source dataset
uspto-grants-2014_08
Patent number
US08796296B2

Reaction notes

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