Water → 3-(4-Nitro-1-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione

HRID 1525632Notes

Reaction equation

HRID 1525632 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][N:7]([CH:14]([CH2:20][C:21](O)=O)[C@@H:15](C(=O)N)[NH2:16])[C:8]2=[O:13])([O-:3])=[O:2].S(Cl)(Cl)=O.[OH2:28].[C:29](=O)([O-])[O-:30].[Na+].[Na+]>CN(C)C=O.CO>[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][N:7]([CH:14]1[CH2:20][CH2:21][C:29](=[O:30])[NH:16][C:15]1=[O:28])[C:8]2=[O:13])([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 24386Thionyl ChlorideHCID 668236033-(4-nitro-1,3-dihydro-1-oxo-2H-isoindol-2-yl)-isoglutamine

Product 1

HCID 114717813-(4-Nitro-1-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dioneYield 78%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 3-(4-nitro-1,3-dihydro-1-oxo-2H-isoindol-2-yl)-isoglutamine (9 g) in N,N-dimethylformamide (80 ml), was added thionyl chloride (6.6 g) by droplet below 0° C. for stirred reaction in heat preservation for 2˜3 hours. The resulting solution was added by droplet into mixture of ice and water and pH value was adjusted to 7˜8 with sodium carbonate. The mixture was stirred for 30 minutes and filtered to get light yellow crude. Refining with methanol gave 6.6 g of target yield as a light yellow solid. yield: 78%.

Workup

  1. customby droplet below 0° C.
  2. customreaction in heat preservation for 2˜3 hours
  3. stirringThe mixture was stirred for 30 minutes
  4. filtrationfiltered
  5. customto get light yellow crude
  6. customyield as a light yellow solid

Sources & evidence

ORD record
ord-ada64fb8a7b341ab829e2e504fffa13c
Source dataset
uspto-grants-2015_07
Patent number
US09085530B2

Reaction notes

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