HCID 86590255, compound → HCID 11030629, compound

HRID 2105749Notes

Reaction equation

HRID 2105749 reaction equation
[CH3:1][C:2]1([CH3:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH3:12])([CH3:11])[NH+:3]1[O-:13]>C(O)C.O=[Pt]=O>[OH:13][N:3]1[C:2]([CH3:14])([CH3:1])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]1([CH3:12])[CH3:11]

Participants

4

Reactant 1

HCID 86590255HCID 86590255, compound

Product 1

HCID 11030629HCID 11030629, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

6.6 g (0.035 mol) of 1,1,3,3-tetramethyl-1,3-dihydroisoindole N-oxide are hydrogenated to saturation in 66 ml of ethanol over 0.12 g of PtO2 at atmospheric pressure. The catalyst is filtered off and the solvent is evaporated on a rotary evaporator, after which the crystalline residue is recrystallized from a little dichloromethane. This gives 5.2 g (78%) of N-hydroxy-1,1,3,3-tetramethyl-1,3-dihydroisoindole which is obtained in the form of colourless crystals; melting point: 128-130° C.

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe solvent is evaporated on a rotary evaporator
  3. customafter which the crystalline residue is recrystallized from a little dichloromethane

Sources & evidence

ORD record
ord-65cbabea57f4409daccf7711b56b2c54
Source dataset
uspto-grants-2009_08
Patent number
US07579411B2

Reaction notes

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