HCID 13458134, compound → HCID 13458137, compound

HRID 653073Notes

Reaction equation

HRID 653073 reaction equation
[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH3:10])=[C:6]([O:11][CH2:12][CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=2)[CH:5]=[CH:4][C:3]=1[C:24](=[O:26])[CH3:25]>C(O)C.CN(C)C=O.[Pd]>[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH3:10])=[C:6]([O:11][CH2:12][CH2:13][O:14][C:15]2[CH:16]=[CH:17][C:18]([NH2:21])=[CH:19][CH:20]=2)[CH:5]=[CH:4][C:3]=1[C:24](=[O:26])[CH3:25]

Participants

5

Reactant 1

HCID 13458134HCID 13458134, compound

Product 1

HCID 13458137HCID 13458137, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×HCID 6228DimethylformamideSolvent

Procedure

1-{2-Hydroxy-3-propyl-4-[2-(4-nitrophenoxy)ethoxy]phenyl}ethanone (6.0 g) was dissolved in a mixture of ethanol (250 ml) and dimethylformamide (60 ml) to which was added, under nitrogen, a slurry of palladium on charcoal (500 mg, 5%) in ethanol (50 ml). The suspension was then hydrogenated on a Parr at 60 psi and room temperature for 2 hours. The suspension was filtered over Celite, washed with ethanol and the filtrate evaporated under reduced pressure to give a brown oil. The oil was triturated with water and filtered to give a brown solid. The solid was recrystallised from ethanol to give a cream solid, m.p. 73°-74° C.

Workup

  1. additionwas added, under nitrogen
  2. filtrationThe suspension was filtered over Celite
  3. washwashed with ethanol
  4. customthe filtrate evaporated under reduced pressure
  5. customto give a brown oil
  6. customThe oil was triturated with water
  7. filtrationfiltered
  8. customto give a brown solid
  9. customThe solid was recrystallised from ethanol
  10. customto give a cream solid, m.p. 73°-74° C.

Sources & evidence

ORD record
ord-32c46545bb524241807892518a946932
Source dataset
uspto-grants-1987_06
Patent number
US04675333

Reaction notes

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