(Z)-3-(4-bromo-3-methoxy-phenylamino)-but-2-enoic acid ethyl ester → HCID 178486798, compound
Reaction equation
C(O[C:4](=[O:18])/[CH:5]=[C:6](\[NH:8][C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[C:11]([O:16][CH3:17])[CH:10]=1)/[CH3:7])C>C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>[Br:15][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][C:11]=1[O:16][CH3:17])[N:8]=[C:6]([CH3:7])[CH:5]=[C:4]2[OH:18]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 220 °C
Procedure
A suspension of 6.6 g (21 mmol) of (Z)-3-(4-bromo-3-methoxy-phenylamino)-but-2-enoic acid ethyl ester in 40 ml of Dowtherm A were heated under stirring at 220° C. for 7.5 h after which time TLC analysis indicated completion of the reaction. The mixture was cooled to RT under stirring and the solvent was decanted off. The remaining solid residue was triturated with hexane, filtered off by suction and dried in a high vacuum to give 4.7 g (84%) of the 6-bromo-7-methoxy-2-methyl-quinolin-4-ol as a dark brown solid. EI mass spectrum, m/e: 269 (M calculated for C11H10BrNO2: 269).
Workup
- temperaturewere heated
- customcompletion of the reaction
- temperatureThe mixture was cooled to RT
- stirringunder stirring
- customthe solvent was decanted off
- customThe remaining solid residue was triturated with hexane
- filtrationfiltered off by suction
- customdried in a high vacuum
Sources & evidence
- ORD record
- ord-bc4dceb9038a459384318ab60c49cefd
- Source dataset
- uspto-grants-2004_11
- Patent number
- US06818767B2
Reaction notes
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