Methanesulfonic Acid → 6-methoxy-3,4-dihydroisoquinolin-1(2H)-one

HRID 257068Notes

Reaction equation

HRID 257068 reaction equation
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.CS(O)(=O)=[O:17].[CH3:20][O:21][C:22]1[CH:23]=[C:24]2[C:28](=[CH:29][CH:30]=1)[C:27](=[N:31]O)[CH2:26][CH2:25]2>>[CH3:20][O:21][C:22]1[CH:23]=[C:24]2[C:28](=[CH:29][CH:30]=1)[C:27](=[O:17])[NH:31][CH2:26][CH2:25]2

Participants

4

Reactant 3

HCID 6395Methanesulfonic AcidHCID 14812Phosphorus oxide (P4O10)HCID 2881895-Methoxyindan-1-one oxime

Product 1

HCID 106073926-methoxy-3,4-dihydroisoquinolin-1(2H)-one

Procedure

Phosphorous pentoxide (1.0 g, 7.1 mmol) is added all at once to methanesulfonic acid (10 g, 104.1 mmol) and stirred for 3 hours at room temperature. 5-Methoxy-1-indanone oxime (100 mg, 0.53 mmol) is added in portions, with each portion allowed to dissolve completely before the next is added. The stirred reaction mixture is heated at 100° for 1.5 hours. The reaction is quenched by the addition of saturated sodium bicarbonate (10 ml) and extracted with 3×5 ml dichloromethane. The combined organic layers are dried over magnesium sulfate and concentrated in vacuo to yield the 6-methoxy-1-oxo-1,2,3,4-tetrahydroisoquinoline. Treatment with boron tribromide (see example 1) yields 6-hydroxy-1-oxo-1,2,3,4-tetrahydroisoquinoline.

Workup

  1. dissolutionto dissolve completely before the
  2. additionnext is added
  3. customThe stirred reaction mixture
  4. temperatureis heated at 100° for 1.5 hours
  5. customThe reaction is quenched by the addition of saturated sodium bicarbonate (10 ml)
  6. extractionextracted with 3×5 ml dichloromethane
  7. dry with materialThe combined organic layers are dried over magnesium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2319b16a129345c89bc4666808e167b4
Source dataset
uspto-grants-1993_11
Patent number
US05260316

Reaction notes

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