Cyclohexene → 3-Amino-4-hydroxybenzamide
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
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of 4-hydroxy-3-nitrobenzamide D58 (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
- temperaturewas heated
- temperatureto reflux under argon for 3 hr
- filtrationThe cooled mixture was filtered through celite
- concentrationthe filtrate concentrated to dryness in vacuo
- customto afford a yellow/brown solid
- customThe product was purified by silica gel chromatography
- washeluting with 0-15% 2M ammonia in MeOH/DCM
Sources & evidence
- ORD record
- ord-d3a7baf530cd4f91898cb4a17e95c2d2
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08299257B2
Reaction notes
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