Methanol → 6-Hydroxyindoline

HRID 1657197Notes

Reaction equation

HRID 1657197 reaction equation
[CH3:1][OH:2].FC(F)(F)S(O)(=O)=O.[CH3:11][C:12](O)=O.CO.[CH2:17](Cl)Cl.C([N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])C>C(O)C.C(=O)(O)[O-].[Na+]>[OH:2][C:1]1[CH:24]=[C:23]2[C:11]([CH2:26][CH2:25][NH:22]2)=[CH:12][CH:17]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 62406Trifluoromethanesulfonic acidHCID 21877243DCM MeOH AcOH

Product 1

HCID 5245076-Hydroxyindoline

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a stirred mixture of 5.8 g of the crude acid above, 65 ml of methanol was added dropwise 5 ml of trifluoromethanesulfonic acid. This mixture was stirred and heated under reflux for 12 hr when TLC (silica gel developed with HOAc/MeOH/CH2Cl2 1:5:45 or 10% triethylamine in ethanol) showed little starting material left. The reaction mixture was cooled, diluted with 75 ml of saturated sodium bicarbonate solution and cooled overnight in the refrigerator. The solid was collected to give 4.3 g of still damp black material. This solid was chromatographed on 100 ml of silica gel packed in 5% methanol/methylene chloride. Elution with 200 ml of 10% methanol/methylene chloride gave 2.7 g (theory from 6-hydroxy indoline 5: 5.46 g or 49% for the two steps) of impure product.

Workup

  1. temperatureheated
  2. waitleft
  3. temperatureThe reaction mixture was cooled
  4. temperaturecooled overnight in the refrigerator
  5. customThe solid was collected
  6. customto give 4.3 g of still damp black material
  7. customThis solid was chromatographed on 100 ml of silica gel
  8. washElution with 200 ml of 10% methanol/methylene chloride

Sources & evidence

ORD record
ord-d42c88be9378467b8a476026cc93c304
Source dataset
uspto-grants-1993_10
Patent number
US05256799

Reaction notes

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