Tin atom → 1188412-94-3

HRID 2409499Notes

Reaction equation

HRID 2409499 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[N+:11]([O-])=O)[C:7](=O)[NH:6][C:5]2=[O:15].[Sn]>CCO>[NH2:11][C:10]1[CH:9]=[C:8]2[C:4](=[CH:3][C:2]=1[NH2:1])[C:5](=[O:15])[NH:6][CH2:7]2

Participants

4

Reactant 2

HCID 5352426Tin atomHCID 151445685-Amino-6-nitro-1H-isoindole-1,3(2H)-dione

Product 1

HCID 686503571188412-94-3Yield 95.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5-Amino-6-nitroisoindoline-1,3-dione (1.0 g, 4.83 mmol) and tin powder (5.8 g, 48.3 mmol) in EtOH (30 mL) was heated at 90° C. for 4 h. The reaction mixture was cooled to RT, filtered the precipitated solid, washed with EtOH (10 mL) and dried to afford 5,6-diaminoisoindolin-1-one (0.75 g, 95%) as a yellow solid. LCMS: 164 (M+1). 1H NMR (300 MHz, DMSO-d6): δ 4.25 (s, 2H); 7.93 (s, 1H), 7.41 (s, 1H); 8.22 (s, 1H); 9.0 (br.s, 4H).

Workup

  1. filtrationfiltered the precipitated solid
  2. washwashed with EtOH (10 mL)
  3. customdried

Sources & evidence

ORD record
ord-98a3777b53ab40cca15e3a4fb7fa889f
Source dataset
uspto-grants-2014_08
Patent number
US08815906B2

Reaction notes

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