Dichloromethane → HCID 12043850, compound

HRID 991451Notes

Reaction equation

HRID 991451 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH3:12])[N:8]=[C:7]1[N:13]([CH2:23][CH2:24][N:25]([CH3:27])[CH3:26])[C:14]3[CH:15]=[CH:16][C:17]([N+:20]([O-])=O)=[CH:18][C:19]=3[C:6]1=[N:5]2.[H][H].C(Cl)Cl>CC(N(C)C)=O.[Pd]>[NH2:20][C:17]1[CH:16]=[CH:15][C:14]2[N:13]([CH2:23][CH2:24][N:25]([CH3:27])[CH3:26])[C:7]3[C:6]([C:19]=2[CH:18]=1)=[N:5][C:4]1[C:9](=[CH:10][C:11]([CH3:12])=[C:2]([CH3:1])[CH:3]=1)[N:8]=3

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 12043849HCID 12043849, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 12043850HCID 12043850, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 31374DimethylacetamideSolvent2×

Procedure

A suspension of 3.63 g (10 mmol) of (2d) and 0.36 g 10% Pd/C in 160 ml DMA was left under 2.7 atm hydrogen pressure for 24 h. The product was soluble in DMA. Pd/C was filtered away with celite. The filtrate was poured onto ice-water and pH was increased to basic with 20% KOH, which resulted in a brown precipitate. The precipitate was chromatographied in 20% MeoH/CH2Cl2, which resulted in 2.80 g of the product (3d).

Workup

  1. filtrationPd/C was filtered away with celite
  2. additionThe filtrate was poured onto ice-water and pH
  3. temperaturewas increased to basic with 20% KOH, which
  4. customresulted in a brown precipitate

Sources & evidence

ORD record
ord-fd0b91464f8142078d50f2763337d074
Source dataset
uspto-grants-2002_10
Patent number
US06465466B1

Reaction notes

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