This is just an idea at this stage. Any feedback is welcome.
1. Photolysis of acetaminophen https://link.springer.com/article/10.1039/c2pp25341k
2. Methylation of 2-amino and 3-hydroxy groups using methyl iodide
3. Alpha keto chlorination. I'm guessing this will chlorinate the 4 position as well? https://sci-hub.se/10.1080/00397910500334637
4. Aminiation
5. Reduction of ketone. I don't think this will reduce the 4-Cl group?
(1) can also be used to produce 3-oxo-5-hydroxy-indoline. Which can probably form indoles through an aldol condensation or grignard reaction.
1. Photolysis of acetaminophen https://link.springer.com/article/10.1039/c2pp25341k
2. Methylation of 2-amino and 3-hydroxy groups using methyl iodide
3. Alpha keto chlorination. I'm guessing this will chlorinate the 4 position as well? https://sci-hub.se/10.1080/00397910500334637
4. Aminiation
5. Reduction of ketone. I don't think this will reduce the 4-Cl group?
(1) can also be used to produce 3-oxo-5-hydroxy-indoline. Which can probably form indoles through an aldol condensation or grignard reaction.