Sodium Thiosulfate → 7-Amino-4-bromo-2-methylisoindolin-1-one

HRID 511234Notes

Reaction equation

HRID 511234 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[NH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:18]=1[C:17](=[O:19])[N:16]([CH3:20])[CH2:15]2.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl>[NH2:9][C:10]1[CH:11]=[CH:12][C:13]([Br:8])=[C:14]2[C:18]=1[C:17](=[O:19])[N:16]([CH3:20])[CH2:15]2

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 67184N-bromobutanimideHCID 450887127-Amino-2-methyl-2,3-dihydro-1H-isoindol-1-one

Product 1

HCID 534084597-Amino-4-bromo-2-methylisoindolin-1-oneYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

NBS (2.3 g, 12.96) was added to a cold (−8° C. to −10° C.) solution of 7-amino-2-methyl-2,3-dihydro-1H-isoindol-1-one (2 g, 12.4 mmol) in DCM (40 mL) and the mixture stirred at −8° C. to −10° C. for 1 h. A solution of 10% aq. sodium thiosulfate (30 mL) was then added to the reaction mixture and stirring was continued for another 20 minutes. The layers were separated and the aqueous layer was extracted with DCM (2×20 mL). The combined organic extracts were washed with water (3×40 mL) and brine (30 mL), and the organic layer was dried (Na2SO4) and concentrated in vacuo to yield 3.2 g of crude product. This material was triturated with ethyl acetate (10 mL) to give 2.2 g of pure 7-amino-4-bromo-2-methyl-2,3-dihydro-1H-isoindol-1-one (XXXIX, yield: 74%).

Workup

  1. stirringstirring
  2. waitwas continued for another 20 minutes
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with DCM (2×20 mL)
  5. washThe combined organic extracts were washed with water (3×40 mL) and brine (30 mL)
  6. dry with materialthe organic layer was dried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customto yield 3.2 g of crude product
  9. customThis material was triturated with ethyl acetate (10 mL)

Sources & evidence

ORD record
ord-dce05f2931924cd5b91ef7ab2c91aa50
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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