Methanol → HCID 178419599, compound
Reaction equation
B(Br)(Br)[Br:2].[C:5]([CH2:9][CH2:10][C:11]1[C:20]2[C:15](=[C:16]([O:25][CH3:26])[C:17]([O:23]C)=[C:18]([O:21]C)[CH:19]=2)[C:14]([CH3:27])=[N:13][C:12]=1[OH:28])([O:7]C)=[O:6].CO>C(Cl)Cl>[BrH:2].[C:5]([CH2:9][CH2:10][C:11]1[C:20]2[C:15](=[C:16]([O:25][CH3:26])[C:17]([OH:23])=[C:18]([OH:21])[CH:19]=2)[C:14]([CH3:27])=[N:13][C:12]=1[OH:28])([OH:7])=[O:6]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -50 °C
Procedure
Boron tribromide (25.0 grams, 99.8 mmol) was added dropwise to a solution of 2.14 grams 4-carbomethoxyethyl-3-hydroxy-6,7,8-trimethoxy-1-methylisoquinoline (6.38 mmol) (Compound J) in 35 ml methylene chloride cooled to -50° C. (in a dry ice-acetone slush bath) under a nitrogen atmosphere. A gummy residue formed immediately. The reaction mixture was warmed to room temperature, stirred for 4 hours and then was cooled to 0°-5° C. Methanol (30 ml) was added dropwise over a 45 minute period and a clear solution was obtained. The solvent was removed in vacuo to provide a brown solid residue which was triturated with ether for 64 hours and then filtered. The solid was washed with ether and dried in vacuo at room temperature to provide 2.14 grams of Compound N (89.7% yield) having a melting point of 172° to 174° C.
Workup
- customA gummy residue formed immediately
- temperatureThe reaction mixture was warmed to room temperature
- temperaturewas cooled to 0°-5° C
- customa clear solution was obtained
- customThe solvent was removed in vacuo
- customto provide a brown solid residue which
- customwas triturated with ether for 64 hours
- filtrationfiltered
- washThe solid was washed with ether
- customdried in vacuo at room temperature
Sources & evidence
- ORD record
- ord-9db08f26edb5461cbcd19c2bed9f8252
- Source dataset
- uspto-grants-1989_04
- Patent number
- US04822800
Reaction notes
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