Hydrochloric Acid → 3-Cyano-4-hydroxy-N-methylbenzamide
Reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13]C1C=CC2CCN(C3CCC3)CCC=2C=1)[C:6]([NH:8][CH3:9])=[O:7])#[N:2].B(Br)(Br)Br.O.Cl>ClCCl>[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[OH:13])[C:6]([NH:8][CH3:9])=[O:7])#[N:2]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
3-Cyano-N-methyl-4-(methyloxy)benzamide (E279, Step 2) (346 mg, 1.82 mmol), was dissolved in dry dichloromethane (10 ml), cooled to 0° C. and treated with boron tribromide (1M solution in dichloromethane) (9.11 ml, 9.11 mmol). The mixture was stirred for 30 minutes, allowed to warm to room temperature and stirred for 18 hours. The mixture was cooled in an ice bath, treated with water added dropwise and then allowed to warm to room temperature. The mixture was poured onto 2M hydrochloric acid (10 ml) and extracted with ethyl acetate. The ethyl acetate layers were combined, dried under magnesium sulfate and evaporated in vacuo. The resulting residue was purified by column chromatography eluting with a mixture of ethyl acetate dichloromethane (1:1) to afford the title compound (86 mg); MS (ES+) m/e 177 [M+H]+.
Workup
- temperatureto warm to room temperature
- stirringstirred for 18 hours
- temperatureThe mixture was cooled in an ice bath
- additionadded dropwise
- temperatureto warm to room temperature
- extractionextracted with ethyl acetate
- customdried under magnesium sulfate
- customevaporated in vacuo
- customThe resulting residue was purified by column chromatography
- washeluting with a mixture of ethyl acetate dichloromethane (1:1)
Sources & evidence
- ORD record
- ord-a6209153ea4a48598ebbbf5318e4e654
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07704994B2
Reaction notes
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