HCID 14401596, compound → 1095-78-9

HRID 1649965Notes

Reaction equation

HRID 1649965 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:11]([C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-])=O)=[C:22]([NH2:29])[CH:21]=2)([C:16]([F:19])([F:18])[F:17])[C:12]([F:15])([F:14])[F:13])[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O.[H][H]>C(OCC)(=O)C.[Pd]>[NH2:29][C:22]1[CH:21]=[C:20]([C:11]([C:4]2[CH:5]=[CH:6][C:7]([NH2:8])=[C:2]([NH2:1])[CH:3]=2)([C:12]([F:13])([F:14])[F:15])[C:16]([F:17])([F:18])[F:19])[CH:25]=[CH:24][C:23]=1[NH2:26]

Participants

5

Reactant 2

HCID 14401596HCID 14401596, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 30836791095-78-9

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

96.7 g (0.23 mol) of 2,2-bis-(3-amino-4-nitrophenyl) hexafluoropropane are dissolved in 1,000 ml of ethyl acetate and reduced with hydrogen (100 bar) at 25° C. in an autoclave after the addition of 3 g of a palladium/charcoal catalyst (5% Pd). After filtering off the catalyst, the ethyl acetate is separated off on the rotary evaporator. The residue is taken up using 1 1 of water and adjusted to a pH of 1 using 1:1 hydrochloric acid. The mixture is then heated to 70°-80° C., 20 g of activated charcoal are added, the mixture is stirred at 70°-80° C. for 15 minutes and the activated charcoal is filtered off. The colorless filtrate is saturated with nitrogen and is adjusted at 10°-20° C. to a pH of 7 using 1:1 ammonia solution under inert gas. The precipitate is separated off, washed well with water and dried to constant weight under reduced pressure. Yield 74 g (0.20 mol); gas chromatographic purity above 99.9%; white solid; m.p. 218°-220° C.

Workup

  1. filtrationAfter filtering off the catalyst
  2. customthe ethyl acetate is separated off on the rotary evaporator
  3. temperatureThe mixture is then heated to 70°-80° C.
  4. addition20 g of activated charcoal are added
  5. filtrationthe activated charcoal is filtered off
  6. customis adjusted at 10°-20° C. to a pH of 7
  7. customThe precipitate is separated off
  8. washwashed well with water
  9. customdried to constant weight under reduced pressure

Sources & evidence

ORD record
ord-599ae443e4cb4f26a7dfbd38edd22bfb
Source dataset
uspto-grants-1990_05
Patent number
US04922019

Reaction notes

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