Cyclohexene → 3-Amino-4-hydroxybenzamide

HRID 1968996Notes

Reaction equation

HRID 1968996 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-])=O.C1CCCCC=1>[Pd].C(O)C>[NH2:11][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:2]=1[OH:1])[C:6]([NH2:8])=[O:7]

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 118496324-Hydroxy-3-nitrobenzamide

Product 1

HCID 224112243-Amino-4-hydroxybenzamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4-hydroxy-3-nitrobenzamide D125 (0.49 g, 2.69 mmol), cyclohexene (1.105 g, 13.45 mmol) and 10% palladium on carbon (0.143 g, 0.135 mmol) in ethanol (20 mL) was heated to reflux under argon for 3 hr. The cooled mixture was filtered through celite and the filtrate concentrated to dryness in vacuo to afford a yellow/brown solid. The product was purified by silica gel chromatography eluting with 0-15% 2M ammonia in MeOH/DCM. The title compound was isolated as a pale brown powder, 0.26 g, 57.2%.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under argon for 3 hr
  3. filtrationThe cooled mixture was filtered through celite
  4. concentrationthe filtrate concentrated to dryness in vacuo
  5. customto afford a yellow/brown solid
  6. customThe product was purified by silica gel chromatography
  7. washeluting with 0-15% 2M ammonia in MeOH/DCM

Sources & evidence

ORD record
ord-3a500fd286c1450d88ae6174d353910b
Source dataset
uspto-grants-2013_04
Patent number
US08426443B2

Reaction notes

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