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

HRID 1411427Notes

Reaction equation

HRID 1411427 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-d9feebf9b35a421ca63268a0339f7ad6
Source dataset
uspto-grants-2014_12
Patent number
US08921514B2

Reaction notes

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