Ammonium Acetate → 6-Methoxyisoquinolin-1-amine
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](OC1C=CC=CC=1)=[N:8][CH:7]=[CH:6]2.C([O-])(=O)C.[NH4+:24]>[OH-].[Na+]>[NH2:24][C:9]1[C:10]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:12][CH:11]=2)[CH:6]=[CH:7][N:8]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 150 °C
Procedure
A mixture of 6-methoxy-1-phenoxyisoquinoline (21.3 g, 85 mmol) and ammonium acetate (55 g) was heated, under a nitrogen atmosphere, to 150° C. and stirred overnight. The mixture was allowed to cool to ambient temperature, after which 3 N sodium hydroxide (280 ml) was added with stirring. The thus obtained solution was extracted with ethyl acetate (2×300 ml) and the combined organic layers were extracted with 2N hydrochloric acid (100 ml). Subsequently, the pH of the aqueous layer was adjusted to 12 with 2 N sodium hydroxide. Extraction with ethyl acetate (300 ml) then afforded an organic layer, which was washed with brine (100 ml), dried (magnesium sulphate) and concentrated under reduced pressure to give 1-amino-6-methoxyisoquinoline (11 g, 75%), ESI-MS: 175.2 [M+H]+
Workup
- temperatureto cool to ambient temperature
- stirringwith stirring
- extractionThe thus obtained solution was extracted with ethyl acetate (2×300 ml)
- extractionthe combined organic layers were extracted with 2N hydrochloric acid (100 ml)
- extractionExtraction with ethyl acetate (300 ml)
- customthen afforded an organic layer, which
- washwas washed with brine (100 ml)
- dry with materialdried (magnesium sulphate)
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-d3eefdaaef254d0b9b711fc2b2645564
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07893088B2
Reaction notes
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