Dichloromethane → HCID 71743933, compound

HRID 2401456Notes

Reaction equation

HRID 2401456 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][N:8]([CH3:13])[C:9]2=[O:12])=[CH:5][C:4]=1[N+:14]([O-])=O.O.O.Cl[Sn]Cl.C(Cl)Cl.[OH-].[Na+]>C(O)C.O>[NH2:14][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][C:3]=1[O:2][CH3:1])[C:9](=[O:12])[N:8]([CH3:13])[CH2:7]2

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 86687918HCID 86687918, compound

Product 1

HCID 71743933HCID 71743933, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

To 6-methoxy-2-methyl-5-nitroisoindolin-1-one (111 mg, 0.5 mmol) in ethanol (6 mL) and water (0.6 mL) was added SnCl2.2H2O (451 mg, 2 mmol) and the mixture was heated to 65° C. for 5 h. DCM (20 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 5-amino-6-methoxy-2-methylisoindolin-1-one (68 mg, 71%) as an off-white solid. LCMS (10 cm_ESCI_Formic_MeCN): [M+H]+=193 at 2.32 min. 1H NMR (400 MHz, DMSO): δ 7.01 (s, 1H), 6.74 (s, 1H), 5.44 (br s, 2H), 4.24 (s, 2H), 3.85 (s, 3H), 3.02 (s, 3H).

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-e0253f6d773e49b592a9470fd95508b0
Source dataset
uspto-grants-2014_08
Patent number
US08796296B2

Reaction notes

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