5,5'-Dichloro-3,3'-dinitro(1,1'-biphenyl)-2,2'-diol → 3,3'-Diamino[1,1'-biphenyl]-2,2'-diol

HRID 733383Notes

Reaction equation

HRID 733383 reaction equation
[CH:1]1[C:2](Cl)=[CH:3][C:4]([N+:19]([O-])=O)=[C:5]([OH:18])[C:6]=1[C:7]1[CH:8]=[C:9](Cl)[CH:10]=[C:11]([N+:14]([O-])=O)[C:12]=1[OH:13]>O1CCCC1.C(N(CC)CC)C.[Pd]>[OH:13][C:12]1[C:11]([NH2:14])=[CH:10][CH:9]=[CH:8][C:7]=1[C:6]1[CH:1]=[CH:2][CH:3]=[C:4]([NH2:19])[C:5]=1[OH:18]

Participants

5

Reactant 1

HCID 52845865,5'-Dichloro-3,3'-dinitro(1,1'-biphenyl)-2,2'-diol

Product 1

HCID 129647533,3'-Diamino[1,1'-biphenyl]-2,2'-diol

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

10 g of niclofolan (1) are dissolved in 100 ml of tetrahydrofuran (THF) and 17.6 g of triethylamine. After addition of 4 g of palladium on carbon 5% and a further 4 g after 40 hours, hydrogenation is carried out to saturation over a total period of about 88 hours. The solution is filtered through Hyflo and is immediately processed further without evaporation. Assumed yield of (2): 100%. Rf 0.11 (CH2Cl2/methanol/NH4OH 25% (60:10:1))

Workup

  1. waithydrogenation is carried out to saturation over a total period of about 88 hours
  2. filtrationThe solution is filtered through Hyflo
  3. customis immediately processed further without evaporation

Sources & evidence

ORD record
ord-353f64cf91c94276ae04a4286c41a9b7
Source dataset
uspto-grants-2009_09
Patent number
US07589196B2

Reaction notes

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