Dichloromethane → 5-Amino-6-chloro-2-methylisoindolin-1-one

HRID 2401469Notes

Reaction equation

HRID 2401469 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][N:7]([CH3:12])[C:8]2=[O:11])=[CH:4][C:3]=1[N+:13]([O-])=O.O.O.Cl[Sn]Cl.C(Cl)Cl.[OH-].[Na+]>C(O)C.O>[NH2:13][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:2]=1[Cl:1])[C:8](=[O:11])[N:7]([CH3:12])[CH2:6]2

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 866879266-Chloro-2,3-dihydro-2-methyl-5-nitro-1H-isoindol-1-one

Product 1

HCID 717439325-Amino-6-chloro-2-methylisoindolin-1-oneYield 85.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

To 6-chloro-2-methyl-5-nitroisoindolin-1-one (340 mg, 1.5 mmol) in ethanol (9 mL) and water (0.9 mL) was added SnCl2.2H2O (1.35 g, 6 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-chloro-2-methylisoindolin-1-one (251 mg, 85%) as an off-white solid. LCMS (10 cm_ESCI_Bicarb_MeCN): [M+H]+=197 at 2.31 min. 1H NMR (400 MHz, d6-DMSO): δ 7.45 (s, 1H), 6.90 (s, 1H), 5.99 (br s, 2H), 4.32 (s, 2H), 3.01 (s, 3H).

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-91b4c26dd7f0482eb52b1587d4413220
Source dataset
uspto-grants-2014_08
Patent number
US08796296B2

Reaction notes

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