Methanol → Methyl 3-amino-5-cyano-2-hydroxybenzoate
Reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([N+:14]([O-])=O)[C:6]([OH:13])=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9])#[N:2].CO>[Pd].O1CCCC1>[NH2:14][C:5]1[C:6]([OH:13])=[C:7]([CH:12]=[C:3]([C:1]#[N:2])[CH:4]=1)[C:8]([O:10][CH3:11])=[O:9]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
To a mixture of 2.71 g of methyl 5-cyano-2-hydroxy-3-nitrobenzoate in a 60 ml of methanol and 40 ml of tetrahydrofuran was added palladium on carbon (500 mg, 10% wet). This suspension was purged with, and stirred under, an atmosphere of hydrogen (via balloon) for 4 h at 50° C. The mixture was then filtered through a plug of Celite, eluting with ethyl acetate (75 ml). The eluent was concentrated in vacuo and the residue was taken up in ethyl acetate (50 ml) and methanol (as needed to dissolve) and was then filtered through a plug of silica gel. The eluent was concentrated in vacuo again and purified via column chromatography using a Biotage Horizon, 65i column, eluting with 1 column volume of 100% hexanes followed by a gradient of 0 to 100% ethyl acetate in hexanes over 10 column volumes, followed by 2 column volumes of 100% ethyl acetate to provide the title compound (1.83 g, 78%). Mass spectrum (ESI) 190.9 (M−1).
Workup
- customThis suspension was purged with, and
- filtrationThe mixture was then filtered through a plug of Celite
- washeluting with ethyl acetate (75 ml)
- concentrationThe eluent was concentrated in vacuo
- filtrationmethanol (as needed to dissolve) and was then filtered through a plug of silica gel
- concentrationThe eluent was concentrated in vacuo again
- custompurified via column chromatography
- washeluting with 1 column volume of 100% hexanes
Sources & evidence
- ORD record
- ord-e598f3375b364aef9407cea2dc470fea
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08445480B2
Reaction notes
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