Hydrazine hydrate (1:1) → 3-Amino-4-hexylbenzoic acid morpholide

HRID 1939294Notes

Reaction equation

HRID 1939294 reaction equation
[CH2:1]([C:7]1[CH:20]=[CH:19][C:10]([C:11]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[O:12])=[CH:9][C:8]=1[N+:21]([O-])=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].O.NN>C(O)C.[Pd]>[NH2:21][C:8]1[CH:9]=[C:10]([CH:19]=[CH:20][C:7]=1[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[C:11]([N:13]1[CH2:14][CH2:15][O:16][CH2:17][CH2:18]1)=[O:12]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 540077734-Hexyl-3-nitrobenzoic acid morpholide

Product 1

HCID 539494553-Amino-4-hexylbenzoic acid morpholideYield 99.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Conditions

Temperature
50 °C

Procedure

The compound ([5]-(54)-75) (700 mg) prepared in Example 62 was dissolved in ethanol (35 ml). After the solution was heated to 50° C., a suspension of 10% Pd/C (70 mg) in ethanol was added, and hydrazine monohydrate (0.35 ml) was added to the solution. The solution was stirred at 50° C. for 30 minutes. After the reaction was completed, the solution was filtered through celite 545 to remove the catalyst. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (Kieselgel 60=20 g, ethyl acetate) to obtain the above-captioned compound ([5]-(55)-75) (631 mg) as colorless oil.

Workup

  1. additionwas added
  2. filtrationthe solution was filtered through celite 545
  3. customto remove the catalyst
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (Kieselgel 60=20 g, ethyl acetate)

Sources & evidence

ORD record
ord-a7ad1755aa984495bb4176776eb2a7d2
Source dataset
uspto-grants-1997_12
Patent number
US05696118

Reaction notes

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