1-Bromopentane → HCID 19363268, compound

HRID 850449Notes

Reaction equation

HRID 850449 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-])=O)[C:5]([OH:7])=[O:6].C(=O)([O-])[O-].[K+].[K+].[CH2:20](Br)[CH2:21][CH2:22][CH2:23][CH3:24]>CN(C=O)C>[NH2:11][C:10]1[CH:9]=[CH:8][C:4]([C:5]([O:7][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[O:6])=[CH:3][C:2]=1[O:1][CH2:9][CH2:10][CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 80571-BromopentaneHCID 11430Potassium CarbonateHCID 692653-Hydroxy-4-nitrobenzoic acid

Product 1

HCID 19363268HCID 19363268, compoundYield 142.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

3-Hydroxy-4-nitrobenzoic acid (5 g, 27.4 mmol), DMF (40 ml), potassium carbonate (13.8 g, 100 mmol) and pentyl bromide (8.7 ml, 70 mmol) were mixed, and this solution was stirred at 100° C. for 1.5 hours. The reaction mixture was filtered to remove the inorganic salt, and DMF was evaporated under reduced pressure. Ethyl acetate (100 ml) was added to the obtained residue, and the mixture was washed 3 times with saturated brine (30 ml) and dried over anhydrous magnesium sulfate. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure. Ethanol (150 ml) and 10% palladium carbon catalyst (0.5 g) were added to the obtained residue, and the mixture was stirred at room temperature for 5.5 hours in a stream of hydrogen. The palladium-carbon catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography (hexane/ethyl acetate=5/1) to give pentyl 4-amino-3-pentyloxybenzoate (5.72 g, 70% in 2 steps) as a pale-yellow oil.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove the inorganic salt, and DMF
  3. customwas evaporated under reduced pressure
  4. additionEthyl acetate (100 ml) was added to the obtained residue
  5. washthe mixture was washed 3 times with saturated brine (30 ml)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationThe drying agent was filtered off
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. additionEthanol (150 ml) and 10% palladium carbon catalyst (0.5 g) were added to the obtained residue
  10. stirringthe mixture was stirred at room temperature for 5.5 hours in a stream of hydrogen
  11. filtrationThe palladium-carbon catalyst was filtered off
  12. concentrationthe filtrate was concentrated under reduced pressure
  13. customThe obtained residue was purified by column chromatography (hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-c99ab1739943485dbaf9cc36d226f3ae
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

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