N-Hydroxyphthalimide → N-(4-quinolyl)methoxyphthalimide

HRID 1271778Notes

Reaction equation

HRID 1271778 reaction equation
[OH:1][CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[CH:5][CH:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[N:33]1[C:37](=[O:38])[C:36]2=[CH:39][CH:40]=[CH:41][CH:42]=[C:35]2[C:34]1=[O:43].CCOC(/N=N/C(OCC)=O)=O>C1COCC1.CCOCC>[N:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]([CH2:2][O:1][N:33]2[C:34](=[O:43])[C:35]3=[CH:42][CH:41]=[CH:40][CH:39]=[C:36]3[C:37]2=[O:38])=[CH:4][CH:5]=1

Participants

7

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 804794-(Hydroxymethyl)quinolineHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 22131435N-(4-quinolyl)methoxyphthalimideYield 88.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-(hydroxymethyl)quinoline (1.20 g, 7.55 mmol), triphenyl phosphine (2.27 g, 8.66 mmol, 1.15 equiv) and N-hydroxyphthalimide (1.42 g, 8.71 mmol, 1.15 equiv) were dissolved in 40 mL of dry THF. Diethylazodicarboxylate (1.44 mL, 9.15 mmol, 1.21 equiv) was then added dropwise and the reaction was stirred overnight. The reaction mixture was then diluted with 50 mL of Et2O and filtered. The resulting solid was dissolved in dichloromethane and washed with 1N NaOH, H2O and brine. The organic portion was dried over Na2SO4 and concentrated under reduced pressure to give the title compound (2.03 g) as a fluffy white solid. MS(CI) m/e 305 (M+H)+.

Workup

  1. filtrationfiltered
  2. dissolutionThe resulting solid was dissolved in dichloromethane
  3. washwashed with 1N NaOH, H2O and brine
  4. dry with materialThe organic portion was dried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bf70735d378c4855abf68a9ef023c527
Source dataset
uspto-grants-2007_04
Patent number
USRE039591E1

Reaction notes

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