Sodium Carbonate → 5,6,7,8-Tetrahydroisoquinoline 2-oxide

HRID 1790492Notes

Reaction equation

HRID 1790492 reaction equation
[CH:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][N:2]=1.C(=O)([O-])[O-:12].[Na+].[Na+].ClC1C=CC=C(C(OO)=O)C=1>C(Cl)Cl>[CH:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][N+:2]=1[O-:12]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 1190105,6,7,8-Tetrahydroisoquinoline

Product 1

HCID 140842165,6,7,8-Tetrahydroisoquinoline 2-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5,6,7,8-Tetrahydroisoquinoline (10 g) was added to methylene chloride (100 ml) and a 10% aqueous solution (100 ml) of sodium carbonate. Under vigorous stirring, a 70% solution of m-chloroperbenzoic acid (20 g) in methylene chloride (100 ml) was dropped thereinto at 0° C. Then the reaction solution was extracted with methylene chloride. The methylene chloride layer was washed with brine, dried and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system) to give the title compound (7.50 g) as a colorless oil. (283-2) 5,6,7,8-Tetrahydroisoquinolin-5-ol

Workup

  1. customat 0° C
  2. extractionThen the reaction solution was extracted with methylene chloride
  3. washThe methylene chloride layer was washed with brine
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system)

Sources & evidence

ORD record
ord-aeeb489cee824a02859ed9c14567ecc3
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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