HCID 19830006, compound → HCID 14986929, compound

HRID 1493588Notes

Reaction equation

HRID 1493588 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:39])([CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]2[CH2:29][CH2:28][N:27]([C:30]3[CH:35]=[CH:34][C:33]([N+:36]([O-])=O)=[CH:32][CH:31]=3)[CH2:26][CH2:25]2)=[CH:20][CH:19]=1)[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1>C(O)(=O)C.[Pd]>[NH2:36][C:33]1[CH:34]=[CH:35][C:30]([N:27]2[CH2:28][CH2:29][N:24]([C:21]3[CH:22]=[CH:23][C:18]([O:17][CH2:16][C:9]([C:3]4[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=4[Cl:1])([OH:39])[CH2:10][N:11]4[CH:15]=[N:14][CH:13]=[N:12]4)=[CH:19][CH:20]=3)[CH2:25][CH2:26]2)=[CH:31][CH:32]=1

Participants

4

Reactant 1

HCID 19830006HCID 19830006, compound

Product 1

HCID 14986929HCID 14986929, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

The product of part (i) (3.0 g, 5.2 mmole) in acetic acid (50 ml) was hydrogenated over 5% palladium on charcoal (0.3 g) at 25 p.s.i. (172 kPa) for 4 hours. The resulting mixture was filtered, the filtrate concentrated under reduced pressure and the residue partitioned between aqueous sodium carbonate and methylene chloride. The organic phase was separated and the aqueous phase further extracted with methylene chloride. The combined organic extracts were dried over magnesium sulphate and evaporated under reduced pressure to provide a foam. Trituration with petroleum ether (40°-60°) yielded the desired product, m.p. 120° (2.8 g, 98%), which was used without further purification.

Workup

  1. filtrationThe resulting mixture was filtered
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customthe residue partitioned between aqueous sodium carbonate and methylene chloride
  4. customThe organic phase was separated
  5. extractionthe aqueous phase further extracted with methylene chloride
  6. dry with materialThe combined organic extracts were dried over magnesium sulphate
  7. customevaporated under reduced pressure
  8. customto provide a foam

Sources & evidence

ORD record
ord-34a34e4feeff476395559170ff62ed14
Source dataset
uspto-grants-1991_06
Patent number
US05023258

Reaction notes

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