Tetrahydrofuran → 4,4'-(1-(4-Fluorophenyl)pyrrolidine-2,5-diyl)dibenzene-1,2-diamine

HRID 1429247Notes

Reaction equation

HRID 1429247 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]([C:13]3[CH:19]=[CH:18][C:16]([NH2:17])=[C:15]([N+:20]([O-])=O)[CH:14]=3)[CH2:11][CH2:10][CH:9]2[C:23]2[CH:29]=[CH:28][C:26]([NH2:27])=[C:25]([N+:30]([O-])=O)[CH:24]=2)=[CH:4][CH:3]=1.C1COCC1>CN(C=O)C.[Pt]=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:9]([C:23]3[CH:24]=[C:25]([NH2:30])[C:26]([NH2:27])=[CH:28][CH:29]=3)[CH2:10][CH2:11][CH:12]2[C:13]2[CH:14]=[C:15]([NH2:20])[C:16]([NH2:17])=[CH:18][CH:19]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 596167834,4'-(1-(4-Fluorophenyl)pyrrolidine-2,5-diyl)bis(2-nitroaniline)

Product 1

HCID 596166404,4'-(1-(4-Fluorophenyl)pyrrolidine-2,5-diyl)dibenzene-1,2-diamine

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 6228DimethylformamideSolvent

Procedure

4,4′-(1-(4-Fluorophenyl)pyrrolidine-2,5-diyl)bis(2-nitroaniline) (0.218 g, 0.50 mmol) was dissolved in DMF (5 mL) then platinum oxide (0.226 g, 0.99 mmol) was added as a THF slurry. The flask was evacuated and purged with nitrogen twice, then evacuated and opened to hydrogen balloon. The mixture was stirred at room temperature for 20 hours. The solution was taken on to the next step without purification.

Workup

  1. customThe flask was evacuated
  2. custompurged with nitrogen twice
  3. customevacuated
  4. customThe solution was taken on to the next step without purification

Sources & evidence

ORD record
ord-9b781ef52b1e483488780f477d5aff50
Source dataset
uspto-grants-2015_01
Patent number
US08937150B2

Reaction notes

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